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Chemistry â€ș Organic Chemistry

Sulfur-Based Synthesis Techniques

Works Count: 32323

Description

This cluster of papers focuses on transition-metal-catalyzed sulfur chemistry, including sulfur bond formation, catalytic coupling reactions, and the synthesis of sulfur-containing compounds. It explores applications in drug design, organic synthesis, thiolation, sulfonylation, and medicinal chemistry.

Keywords

Transition-Metal-Catalyzed; Sulfur Bond Formation; Catalytic Coupling Reactions; Sulfur-Containing Compounds; Drug Design; Organic Synthesis; Thiolation; Sulfonylation; Aryl Halides; Medicinal Chemistry

Tetrahedron report number 163

1984-01-01
James T. Lindley

Cyclopentyl Methyl Ether as a New and Alternative Process Solvent

2007-02-24
Kiyoshi Watanabe , Noriyuki Yamagiwa , Yasuhiro Torisawa
Cyclopentyl methyl ether (CPME) has become available in commercial quantities since November 2005 from Zeon Corporation with approval by the Toxic Substances Control Act (TSCA) and the European List of 
 Cyclopentyl methyl ether (CPME) has become available in commercial quantities since November 2005 from Zeon Corporation with approval by the Toxic Substances Control Act (TSCA) and the European List of Notified Chemical Substances (ELINCS). A high boiling point (106 °C) and preferable characteristics such as low formation of peroxides, relative stability under acidic and basic conditions, formation of azeotropes with water coupled with a narrow explosion range render CPME an alternative to other ethereal solvents such as tetrahydrofuran (THF), 2-methyl tetrahydrofuran (2-MeTHF), dioxane (carcinogenic), and 1,2-dimethoxyethane (DME). Conventional drying is unnecessary for general organometallic reactions including Grignard reactions, enolate formation, Claisen condensation, general reductions, and Pd-based transformations.

Cobalt-Catalyzed Cross-Coupling Reactions

2010-02-11
GĂ©rard Cahiez , Alban Moyeux
ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTCobalt-Catalyzed Cross-Coupling ReactionsGĂ©rard Cahiez* and Alban MoyeuxView Author Information Department of Chemistry (FRE 3043), CNRS-UniversitĂ© de Paris 13, 74 Rue Marcel Cachin, F-93017 Bobigny, France* E-mail: [email 
 ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTCobalt-Catalyzed Cross-Coupling ReactionsGĂ©rard Cahiez* and Alban MoyeuxView Author Information Department of Chemistry (FRE 3043), CNRS-UniversitĂ© de Paris 13, 74 Rue Marcel Cachin, F-93017 Bobigny, France* E-mail: [email protected]Cite this: Chem. Rev. 2010, 110, 3, 1435–1462Publication Date (Web):February 11, 2010Publication History Received28 February 2009Published online11 February 2010Published inissue 10 March 2010https://pubs.acs.org/doi/10.1021/cr9000786https://doi.org/10.1021/cr9000786review-articleACS PublicationsCopyright © 2010 American Chemical SocietyRequest reuse permissionsArticle Views24122Altmetric-Citations558LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Alkyls,Anions,Coupling reactions,Inorganic compounds,Reagents Get e-Alerts

Transition‐Metal‐Catalyzed CïŁżS Bond Coupling Reaction

2014-01-17
Chin‐Fa Lee , Yi‐Chen Liu , Satpal Singh Badsara
Abstract Sulfur‐containing molecules such as thioethers are commonly found in chemical biology, organic synthesis, and materials chemistry. While many reliable methods have been developed for preparing these compounds, harsh reaction 
 Abstract Sulfur‐containing molecules such as thioethers are commonly found in chemical biology, organic synthesis, and materials chemistry. While many reliable methods have been developed for preparing these compounds, harsh reaction conditions are usually required in the traditional methods. The transition metals have been applied in this field, and the palladium‐catalyzed coupling of thiols with aryl halides and pseudo halides is one of the most important methods in the synthesis of thioethers. Other metals have also been used for the same purpose. Here, we summarize recent efforts in metal‐catalyzed CïŁżS bond cross‐coupling reactions, focusing especially on the coupling of thiols with aryl‐ and vinyl halides based on different metals.

Copper-Promoted Sulfenylation of sp<sup>2</sup> C–H Bonds

2012-10-29
Ly D. Tran , Ilya Popov , Olafs Daugulis
An auxiliary-assisted, copper catalyzed or promoted sulfenylation of benzoic acid derivative ÎČ-C–H bonds and benzylamine derivative Îł-C–H bonds has been developed. The method employs disulfide reagents, copper(II) acetate, and DMSO 
 An auxiliary-assisted, copper catalyzed or promoted sulfenylation of benzoic acid derivative ÎČ-C–H bonds and benzylamine derivative Îł-C–H bonds has been developed. The method employs disulfide reagents, copper(II) acetate, and DMSO solvent at 90–130 °C. Application of this methodology to the direct trifluoromethylsulfenylation of C–H bonds was demonstrated.
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A General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols

2006-01-31
Manuel A. Fernández‐Rodríguez , Qilong Shen , John F. Hartwig
A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes 
 A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes of 1 occur in excellent yields with broad scope and exhibit extraordinary turnover numbers and high tolerance of functional groups. Turnover numbers usually exceed those of previous catalysts by 2 or 3 orders of magnitude. In addition, the reactions of aryl tosylates with alkane thiols to form aryl sulfides are reported for the first time. Finally, the synthesis of a diarylsulfide from two bromoarenes was accomplished using a hydrogen sulfide surrogate.

Cobalt-Catalyzed Aryl−Sulfur Bond Formation

2006-11-01
Ying‐Chieh Wong , Thiruvellore Thatai Jayanth , Chien‐Hong Cheng
A new cobalt-catalyzed coupling of aryl halides with thiophenols and alkanethiols is reported. A variety of aryl sulfides can be prepared in excellent yields under mild reaction conditions using 1−2 
 A new cobalt-catalyzed coupling of aryl halides with thiophenols and alkanethiols is reported. A variety of aryl sulfides can be prepared in excellent yields under mild reaction conditions using 1−2 mol % of CoI2(dppe) and Zn. This new cobalt-catalyzed coupling represents an interesting addition to previously known methods to synthesize thioethers.

Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

2011-03-09
I. P. Beletskaya , Valentine P. Ananikov
ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTTransition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition ReactionsIrina P. Beletskaya*‡ and Valentine P. Ananikov*§View Author Information‡ Lomonosov Moscow State University, Chemistry Department, 
 ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTTransition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition ReactionsIrina P. Beletskaya*‡ and Valentine P. Ananikov*§View Author Information‡ Lomonosov Moscow State University, Chemistry Department, Vorob'evy gory, Moscow 119899, Russia§ Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia*E-mail: [email protected]; Fax: +7 (495) 9393618 (Beletskaya). E-mail: [email protected]; Fax: +7 (499) 1355328 (Ananikov).Cite this: Chem. Rev. 2011, 111, 3, 1596–1636Publication Date (Web):March 9, 2011Publication History Received18 October 2010Published online9 March 2011Published inissue 9 March 2011https://pubs.acs.org/doi/10.1021/cr100347khttps://doi.org/10.1021/cr100347kreview-articleACS PublicationsCopyright © 2011 American Chemical SocietyRequest reuse permissionsArticle Views20187Altmetric-Citations1437LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Anions,Catalysts,Cross coupling reaction,Hydrocarbons,Thiols Get e-Alerts

Trifluoromethanesulfonic acid and derivatives

1977-02-01
Richard Howells , J. D. Mc Cown
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTrifluoromethanesulfonic acid and derivativesR. D. Howells and J. D. Mc CownCite this: Chem. Rev. 1977, 77, 1, 69–92Publication Date (Print):February 1, 1977Publication History Published online1 May 2002Published 
 ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTrifluoromethanesulfonic acid and derivativesR. D. Howells and J. D. Mc CownCite this: Chem. Rev. 1977, 77, 1, 69–92Publication Date (Print):February 1, 1977Publication History Published online1 May 2002Published inissue 1 February 1977https://pubs.acs.org/doi/10.1021/cr60305a005https://doi.org/10.1021/cr60305a005research-articleACS PublicationsRequest reuse permissionsArticle Views7712Altmetric-Citations360LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Transfer of Sulfur: From Simple to Diverse

2013-07-11
Hui Liu , Xuefeng Jiang
Abstract The introduction of sulfur atoms onto target molecules is an important area in organic synthesis, in particular in the synthesis of pharmaceutical compounds, and a wide variety of sulfuration 
 Abstract The introduction of sulfur atoms onto target molecules is an important area in organic synthesis, in particular in the synthesis of pharmaceutical compounds, and a wide variety of sulfuration agents have been developed for thionation reactions over the past few decades. In this Focus Review, we collect and summarize the CïŁżS bond‐formation reactions that have been used to construct CïŁżS bonds in natural products and pharmaceutical compounds.

Iron‐Catalyzed S‐Arylation of Thiols with Aryl Iodides

2008-03-03
Arkaitz Correa , MĂłnica Carril , Carsten Bolm
Strike while the iron is hot: An efficient iron-catalyzed protocol for the S-arylation of aromatic and heteroaromatic thiol derivatives has been developed, which involves an inexpensive catalyst system formed by 
 Strike while the iron is hot: An efficient iron-catalyzed protocol for the S-arylation of aromatic and heteroaromatic thiol derivatives has been developed, which involves an inexpensive catalyst system formed by combining FeCl3 and N,Nâ€Č-dimethylethylenediamine at 135 °C. This method avoids the use of expensive and/or air-sensitive ligands and provides in most cases the desired sulfide in high yields.

Recent advances in C–S bond formation via C–H bond functionalization and decarboxylation

2014-10-13
Chao Shen , Pengfei Zhang , Qiang Sun +3 more
The development of mild and general methods for C–S bond formation has received significant attention because the C–S bond is indispensable in many important biological and pharmaceutical compounds. The development of mild and general methods for C–S bond formation has received significant attention because the C–S bond is indispensable in many important biological and pharmaceutical compounds.

A General Palladium-Catalyzed Coupling of Aryl Bromides/Triflates and Thiols

2004-10-28
Takahiro Itoh , Toshiaki Mase
We have developed an efficient palladium-catalyzed carbon-sulfur bond formation reaction of aryl bromides, triflates, and activated aryl chloride. Using this protocol, we have shown tolerance to a wide variety of 
 We have developed an efficient palladium-catalyzed carbon-sulfur bond formation reaction of aryl bromides, triflates, and activated aryl chloride. Using this protocol, we have shown tolerance to a wide variety of aryl thiols and alkyl thiols that can also be used as sulfide equivalents. [reaction: see text]

Desulfonylation reactions: Recent developments

1999-08-01
Carmén Nåjera , Miguel Yus

Metal-Catalyzed Carbon−Sulfur Bond Formation

2000-07-11
Teruyuki Kondo , Take‐aki Mitsudo
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMetal-Catalyzed Carbon−Sulfur Bond FormationTeruyuki Kondo and Take-aki MitsudoView Author Information Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan Cite 
 ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMetal-Catalyzed Carbon−Sulfur Bond FormationTeruyuki Kondo and Take-aki MitsudoView Author Information Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan Cite this: Chem. Rev. 2000, 100, 8, 3205–3220Publication Date (Web):July 11, 2000Publication History Received3 January 2000Published online11 July 2000Published inissue 1 August 2000https://doi.org/10.1021/cr9902749Copyright © 2000 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views11094Altmetric-Citations1126LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (739 KB) Get e-AlertsSUBJECTS:Hydrocarbons,Inorganic carbon compounds,Oxides,Sulfides,Thiols Get e-Alerts

Tri-<i>n</i>-butyltin Hydride as Reagent in Organic Synthesis

1987-01-01
Wilhelm P. Neumann
The considerable growth of the application of tri-n-butyltin hydride (TBTH) in organic synthesis since 1975 is reviewed. Four main aspects are included: a) selective transformation of C-X (X=halide, OH, S, 
 The considerable growth of the application of tri-n-butyltin hydride (TBTH) in organic synthesis since 1975 is reviewed. Four main aspects are included: a) selective transformation of C-X (X=halide, OH, S, Se, NH2, NO2, COOH) to C-H bonds, b) addition to C=C, C≡C, C=Y ( Y = O, S, N) groups, c) use of intermediate carbon centered radicals from a) or b) for intra- or intermolecular C-C coupling, which occurs mostly regio- and stereoselectively, and d) use in palladium-catalyzed syntheses, e.g. of aldehydes. 1. Introduction 2. Dehalogenation 2.1. Replacement of Halogen by Hydrogen or Deuterium at the Same Carbon Atom 2.2. Dehalogenation Followed by Intramolecular C-C Coupling 2.3. Dehalogenation Followed by Intermolecular C-C Coupling 2.4. Dehalogenation Followed by Radical Rearrangements or Fragmentation 2.5. Dehalogenation at Heteroatoms 3. Cleavage of C-O, C-S, C-Se, C-Te Bonds 3.1. Deoxygenation 3.2. Desulfuration 3.3. Deselenation and Detelluration 4. Cleavage of C-N Bonds 4.1. Deamination 4.2. Denitration 5. Decarboxylation 6. Addition to C- C Double and Triple Bonds 7. Addition to Carbonyl and Other C=X Groups 8. Miscellaneous Uses 9. Preparation of Tri-n-butyltin Hydride (Deuteride, Tritide), and Work-up Procedure

The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions

1980-05-01
Toshihiko Migita , T. Shimizu , Yoriyoshi Asami +3 more
Abstract In the presence of a catalytic amount of tetrakis(triphenylphosphine) palladium, phenyl and methyl or methoxyphenyl iodides and bromides were found to react with thiolate anions in alcoholic solvents, to 
 Abstract In the presence of a catalytic amount of tetrakis(triphenylphosphine) palladium, phenyl and methyl or methoxyphenyl iodides and bromides were found to react with thiolate anions in alcoholic solvents, to give the corresponding aryl sulfides in excellent yield. The reaction is useful to prepare symmetrical or unsymmetrical diaryl sulfides and aryl alkyl sulfides. The reaction mechanism does not involve aryl halide radical anions, but is thought to involve oxidative addition of aryl halide to Pd(0), nucleophilic substitution on the adduct followed by reductive elimination.
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Chalcogenides as Organocatalysts

2007-12-01
Eoghan M. McGarrigle , Eddie L. Myers , Ona Illa +3 more
ADVERTISEMENT RETURN TO ISSUEPREVArticleChalcogenides as OrganocatalystsEoghan M. McGarrigle, Eddie L. Myers, Ona Illa, Michael A. Shaw, Samantha L. Riches, and Varinder K. AggarwalView Author Information School of Chemistry, University of 
 ADVERTISEMENT RETURN TO ISSUEPREVArticleChalcogenides as OrganocatalystsEoghan M. McGarrigle, Eddie L. Myers, Ona Illa, Michael A. Shaw, Samantha L. Riches, and Varinder K. AggarwalView Author Information School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, United Kingdom Cite this: Chem. Rev. 2007, 107, 12, 5841–5883Publication Date (Web):December 12, 2007Publication History Received21 August 2007Published online12 December 2007Published inissue 1 December 2007https://pubs.acs.org/doi/10.1021/cr068402yhttps://doi.org/10.1021/cr068402yresearch-articleACS PublicationsCopyright © 2007 American Chemical SocietyRequest reuse permissionsArticle Views8516Altmetric-Citations416LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Aldehydes,Ethers,Salts,Stereoselectivity,Sulfides Get e-Alerts

Moderne Synthesemethoden: Kupfer‐vermittelte C(Aryl)‐O‐, C(Aryl)‐N‐ und C(Aryl)‐S‐VerknĂŒpfungen

2003-11-11
Steven V. Ley , Andrew W. Thomas
Abstract Kupfer‐vermittelte C(Aryl)‐N‐, C(Aryl)‐O‐ und C(Aryl)‐S‐ VerknĂŒpfungen sind Kupplungsreaktionen mit einer großen Bandbreite an Substraten. In dieser Hinsicht ergĂ€nzt diese Methode die Palladium‐vermittelten Arylierungsreaktionen. Hier beschreiben wir neue Entwicklungen bei 
 Abstract Kupfer‐vermittelte C(Aryl)‐N‐, C(Aryl)‐O‐ und C(Aryl)‐S‐ VerknĂŒpfungen sind Kupplungsreaktionen mit einer großen Bandbreite an Substraten. In dieser Hinsicht ergĂ€nzt diese Methode die Palladium‐vermittelten Arylierungsreaktionen. Hier beschreiben wir neue Entwicklungen bei stöchiometrischen und katalytischen Varianten der Reaktionen mit ArylboronsĂ€uren, Arylhalogeniden, Iodoniumsalzen, Siloxanen, Stannanen, Plumbanen, Bismutaten und Trifluoroboraten als Aryldonoren. Erst kĂŒrzlich wurden ArylboronsĂ€uren als Reaktionspartner fĂŒr die O‐ und N‐Arylierung eingefĂŒhrt; dieser Klasse von Aryldonoren wird in diesem Aufsatz besondere Aufmerksamkeit gewidmet. Durch die Verwendung unterschiedlicher Kupferquellen und Basen sowie zusĂ€tzlicher Liganden und Additive konnten deutliche Verbesserungen erzielt werden. Mechanistische Untersuchungen sollen Aufschluss ĂŒber die katalytisch aktiven Spezies geben und so zur Entwicklung milderer Methoden mit grĂ¶ĂŸerer Effizienz fĂŒhren. Der Aufsatz umfasst die Literatur bis Ende April 2003.

Organocatalytic Carbon–Sulfur Bond-Forming Reactions

2014-08-21
Pankaj Chauhan , Suruchi Mahajan , Dieter Enders
ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTOrganocatalytic Carbon–Sulfur Bond-Forming ReactionsPankaj Chauhan, Suruchi Mahajan, and Dieter Enders*View Author Information Institute of Organic Chemistry, RWTH Aachen University Landoltweg 1, 52074 Aachen, Germany*Tel.: +49 241 809 
 ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTOrganocatalytic Carbon–Sulfur Bond-Forming ReactionsPankaj Chauhan, Suruchi Mahajan, and Dieter Enders*View Author Information Institute of Organic Chemistry, RWTH Aachen University Landoltweg 1, 52074 Aachen, Germany*Tel.: +49 241 809 4676. Fax: +49 241 809 2127. E-mail: [email protected]Cite this: Chem. Rev. 2014, 114, 18, 8807–8864Publication Date (Web):August 21, 2014Publication History Received30 April 2014Published online21 August 2014Published inissue 24 September 2014https://pubs.acs.org/doi/10.1021/cr500235vhttps://doi.org/10.1021/cr500235vreview-articleACS PublicationsCopyright © 2014 American Chemical SocietyRequest reuse permissionsArticle Views14195Altmetric-Citations515LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Adducts,Catalysts,Organic compounds,Stereoselectivity,Thiols Get e-Alerts

New synthetic reactions. Sulfenylations and dehydrosulfenylations of esters and ketones

1976-08-01
Barry M. Trost , T. N. SALZMANN , Kunio Hiroi
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNew synthetic reactions. Sulfenylations and dehydrosulfenylations of esters and ketonesBarry M. Trost, Thomas N. Salzmann, and Kunio HiroiCite this: J. Am. Chem. Soc. 1976, 98, 16, 4887–4902Publication 
 ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNew synthetic reactions. Sulfenylations and dehydrosulfenylations of esters and ketonesBarry M. Trost, Thomas N. Salzmann, and Kunio HiroiCite this: J. Am. Chem. Soc. 1976, 98, 16, 4887–4902Publication Date (Print):August 1, 1976Publication History Published online1 May 2002Published inissue 1 August 1976https://pubs.acs.org/doi/10.1021/ja00432a034https://doi.org/10.1021/ja00432a034research-articleACS PublicationsRequest reuse permissionsArticle Views3474Altmetric-Citations444LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Iodine‐Catalyzed Regioselective Sulfenylation of Indoles with Sulfonyl Hydrazides

2013-03-28
Fulai Yang , Shi‐Kai Tian
New S in town: Sulfonyl hydrazides smoothly undergo sulfenylation with indoles in the presence of 10 mol % I2 to give structurally diverse indole thioethers in moderate to excellent yields 
 New S in town: Sulfonyl hydrazides smoothly undergo sulfenylation with indoles in the presence of 10 mol % I2 to give structurally diverse indole thioethers in moderate to excellent yields with extremely high regioselectivity. This study paves the way for the use of sulfonyl hydrazides as unique sulfur electrophiles in chemical synthesis. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Vinyl Sulfones as Mechanism-Based Cysteine Protease Inhibitors

1995-08-01
James T. Palmer , David Rasnick , Jeffrey L. Klaus +1 more
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTVinyl Sulfones as Mechanism-Based Cysteine Protease InhibitorsJames T. Palmer, David Rasnick, Jeffrey L. Klaus, and Dieter BrommeCite this: J. Med. Chem. 1995, 38, 17, 3193–3196Publication Date (Print):August 
 ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTVinyl Sulfones as Mechanism-Based Cysteine Protease InhibitorsJames T. Palmer, David Rasnick, Jeffrey L. Klaus, and Dieter BrommeCite this: J. Med. Chem. 1995, 38, 17, 3193–3196Publication Date (Print):August 1, 1995Publication History Published online1 May 2002Published inissue 1 August 1995https://pubs.acs.org/doi/10.1021/jm00017a002https://doi.org/10.1021/jm00017a002research-articleACS PublicationsRequest reuse permissionsArticle Views3766Altmetric-Citations410LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Thiol Ester−Boronic Acid Coupling. A Mechanistically Unprecedented and General Ketone Synthesis

2000-10-26
Lanny S. Liebeskind , Jiƙí Ơrogl
ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTThiol Ester−Boronic Acid Coupling. A Mechanistically Unprecedented and General Ketone SynthesisLanny S. Liebeskind and Jiri SroglView Author Information Department of Chemistry, Emory University 1515 Pierce Drive, Atlanta, 
 ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTThiol Ester−Boronic Acid Coupling. A Mechanistically Unprecedented and General Ketone SynthesisLanny S. Liebeskind and Jiri SroglView Author Information Department of Chemistry, Emory University 1515 Pierce Drive, Atlanta, Georgia 30322 Cite this: J. Am. Chem. Soc. 2000, 122, 45, 11260–11261Publication Date (Web):October 26, 2000Publication History Received15 September 2000Published online26 October 2000Published inissue 1 November 2000https://pubs.acs.org/doi/10.1021/ja005613qhttps://doi.org/10.1021/ja005613qrapid-communicationACS PublicationsCopyright © 2000 American Chemical SocietyRequest reuse permissionsArticle Views14026Altmetric-Citations554LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Boron,Cross coupling reaction,Ketones,Organic compounds,Thiols Get e-Alerts

A General, Efficient, and Inexpensive Catalyst System for the Coupling of Aryl Iodides and Thiols

2002-09-11
Fuk Yee Kwong , Stephen L. Buchwald
An efficient copper-catalyzed carbon−sulfur bond formation reaction was developed. This method is particularly noteworthy given its experimental simplicity, high generality, and exceptional level of functional group toleration and the low 
 An efficient copper-catalyzed carbon−sulfur bond formation reaction was developed. This method is particularly noteworthy given its experimental simplicity, high generality, and exceptional level of functional group toleration and the low cost of the catalyst system.

Recent applications of arene diazonium salts in organic synthesis

2013-01-01
Fanyang Mo , Guangbin Dong , Yan Zhang +1 more
Arene diazonium salts are common, easily prepared and highly useful intermediates in organic synthesis due to their rich reactivity and diverse transformations. In this review, recent advances involving arene diazonium 
 Arene diazonium salts are common, easily prepared and highly useful intermediates in organic synthesis due to their rich reactivity and diverse transformations. In this review, recent advances involving arene diazonium salts as starting materials or active intermediates for various synthetically useful applications are summarized.

A General Method for the Formation of Aryl−Sulfur Bonds Using Copper(I) Catalysts

2002-07-12
Craig G. Bates , Rattan K. Gujadhur , D. Venkataraman
We report a mild, palladium-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the 
 We report a mild, palladium-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 °C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available iodides and thiols.

Enantioselective Organocatalyzed α Sulfenylation of Aldehydes

2005-01-18
Mauro Marigo , Tobias C. Wabnitz , Doris Fielenbach +1 more
The facile elaboration of optically active α-sulfanyl-substituted aldehydes makes their direct preparation from unmodified aldehydes and 1-benzylsulfanyl-1,2,4-triazole particularly valuable. The substituted aldehydes are formed with excellent enantioselectivities in the presence 
 The facile elaboration of optically active α-sulfanyl-substituted aldehydes makes their direct preparation from unmodified aldehydes and 1-benzylsulfanyl-1,2,4-triazole particularly valuable. The substituted aldehydes are formed with excellent enantioselectivities in the presence of sterically demanding chiral pyrrolidine derivatives as organocatalysts (see scheme). R, Râ€Č=H, alkyl, allyl, benzyl, Ph. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z462101_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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Transition-metal mediated carbon–sulfur bond activation and transformations

2012-10-18
Liandi Wang , Wei He , Zhengkun Yu
C–S bond activation, cleavage and transformations by means of transition metal compounds have recently become more and more important in the petroleum industry and synthetic chemistry. Homogeneous transition metal compounds 
 C–S bond activation, cleavage and transformations by means of transition metal compounds have recently become more and more important in the petroleum industry and synthetic chemistry. Homogeneous transition metal compounds have been investigated in order to provide the fundamental insight into the C–S bond cleavage in problematic organosulfur compounds such as thiophene, benzo- and dibenzothiophene derivatives. Rendering transition-metal mediated reactions with organosulfur compounds catalytic may provide promising routes to deep hydrodesulfurization of petroleum feedstocks, and offer potentially useful synthetic protocols for cross-couplings and biomimetic organic synthesis. During the last few decades increasing work was documented on C–S bond activation and transformations by means of transition metal compounds. This review summarizes the recent advances in C–S bond cleavage via the insertion of transition metals into the inert C–S bonds of these problematic organosulfur compounds, and transition-metal mediated C–S bond transformations via C–S activation through cross-couplings of thioesters, ketene dithioacetals, sulfonyl chlorides, and other diverse organosulfur compounds.

A ÎČ-Keto Ester as a Novel, Efficient, and Versatile Ligand for Copper(I)-Catalyzed C−N, C−O, and C−S Coupling Reactions

2007-04-14
Xin Lv , Weiliang Bao
Employing ethyl 2-oxocyclohexanecarboxylate as a novel, efficient, and versatile ligand, the copper-catalyzed coupling reactions of various N/O/S nucleophilic reagents with aryl halides could be successfully carried out under mild conditions. 
 Employing ethyl 2-oxocyclohexanecarboxylate as a novel, efficient, and versatile ligand, the copper-catalyzed coupling reactions of various N/O/S nucleophilic reagents with aryl halides could be successfully carried out under mild conditions. A variety of products including N-arylamides, N-arylimidazoles, aryl ethers, and aryl thioethers were synthesized in good to excellent yields.

Palladium-Catalyzed α-Arylation of Ketones

1997-11-01
Michael Palucki , Stephen L. Buchwald
ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTPalladium-Catalyzed α-Arylation of KetonesMichael Palucki and Stephen L. BuchwaldView Author Information Department of Chemistry Massachusetts Institute of Technology Cambridge, Massachusetts 02139 Cite this: J. Am. Chem. Soc. 
 ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTPalladium-Catalyzed α-Arylation of KetonesMichael Palucki and Stephen L. BuchwaldView Author Information Department of Chemistry Massachusetts Institute of Technology Cambridge, Massachusetts 02139 Cite this: J. Am. Chem. Soc. 1997, 119, 45, 11108–11109Publication Date (Web):November 12, 1997Publication History Received30 July 1997Published online12 November 1997Published inissue 1 November 1997https://pubs.acs.org/doi/10.1021/ja972593shttps://doi.org/10.1021/ja972593srapid-communicationACS PublicationsCopyright © 1997 American Chemical SocietyRequest reuse permissionsArticle Views13548Altmetric-Citations541LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Anions,Arylation,Ketones,Mixtures,Palladium Get e-Alerts

Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols With Aryl and Heteroaryl Iodides via Thiyl Radicals

2016-01-21
Martins S. Oderinde , Mathieu Frenette , Daniel Robbins +2 more
Ni-catalyzed cross-couplings of aryl, benzyl, and alkyl thiols with aryl and heteroaryl iodides were accomplished in the presence of an Ir-photoredox catalyst. Highly chemoselective C–S cross-coupling was achieved versus competitive 
 Ni-catalyzed cross-couplings of aryl, benzyl, and alkyl thiols with aryl and heteroaryl iodides were accomplished in the presence of an Ir-photoredox catalyst. Highly chemoselective C–S cross-coupling was achieved versus competitive C–O and C–N cross-couplings. This C–S cross-coupling method exhibits remarkable functional group tolerance, and the reactions can be carried out in the presence of molecular oxygen. Mechanistic investigations indicated that the reaction proceeded through transient Ni(I)-species and thiyl radicals. Distinct from nickel-catalyzed cross-coupling reactions involving carbon-centered radicals, control experiments and spectroscopic studies suggest that this C–S cross-coupling reaction does not involve a Ni(0)-species.

Dimethyloxosulfonium Methylide ((CH<sub>3</sub>)<sub>2</sub>SOCH<sub>2</sub>) and Dimethylsulfonium Methylide ((CH<sub>3</sub>)<sub>2</sub>SCH<sub>2</sub>). Formation and Application to Organic Synthesis

1965-03-01
E. J. Corey , Michael Chaykovsky
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDimethyloxosulfonium Methylide ((CH3)2SOCH2) and Dimethylsulfonium Methylide ((CH3)2SCH2). Formation and Application to Organic SynthesisE. J. Corey and Michael ChaykovskyCite this: J. Am. Chem. Soc. 1965, 87, 6, 1353–1364Publication 
 ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDimethyloxosulfonium Methylide ((CH3)2SOCH2) and Dimethylsulfonium Methylide ((CH3)2SCH2). Formation and Application to Organic SynthesisE. J. Corey and Michael ChaykovskyCite this: J. Am. Chem. Soc. 1965, 87, 6, 1353–1364Publication Date (Print):March 1, 1965Publication History Published online1 May 2002Published inissue 1 March 1965https://pubs.acs.org/doi/10.1021/ja01084a034https://doi.org/10.1021/ja01084a034research-articleACS PublicationsRequest reuse permissionsArticle Views15282Altmetric-Citations1393LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

.alpha.-Sulfenylated carbonyl compounds in organic synthesis

1978-08-01
Barry M. Trost
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXT.alpha.-Sulfenylated carbonyl compounds in organic synthesisBarry M. TrostCite this: Chem. Rev. 1978, 78, 4, 363–382Publication Date (Print):August 1, 1978Publication History Published online1 May 2002Published inissue 1 August 
 ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXT.alpha.-Sulfenylated carbonyl compounds in organic synthesisBarry M. TrostCite this: Chem. Rev. 1978, 78, 4, 363–382Publication Date (Print):August 1, 1978Publication History Published online1 May 2002Published inissue 1 August 1978https://pubs.acs.org/doi/10.1021/cr60314a002https://doi.org/10.1021/cr60314a002research-articleACS PublicationsRequest reuse permissionsArticle Views1856Altmetric-Citations388LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Photoredox α-Vinylation of α-Amino Acids and <i>N</i>-Aryl Amines

2014-07-15
Adam Noble , David W. C. MacMillan
A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl 
 A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.
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Dioxygen-Triggered Oxidative Radical Reaction: Direct Aerobic Difunctionalization of Terminal Alkynes toward ÎČ-Keto Sulfones

2013-07-18
Qingquan Lu , Jian Zhang , Ganglu Zhao +3 more
An unprecedented dioxygen-triggered oxidative radical process was explored using dioxygen as the solely terminal oxidant, realizing aerobic oxidaitve difunctionalization of terminal alkynes toward ÎČ-keto sulfones with high selectivity. Operando IR 
 An unprecedented dioxygen-triggered oxidative radical process was explored using dioxygen as the solely terminal oxidant, realizing aerobic oxidaitve difunctionalization of terminal alkynes toward ÎČ-keto sulfones with high selectivity. Operando IR experiments revealed that pyridine not only acts as a base to successfully surpress ATRA (atom transfer radical addition) process, but also plays a vital role in reducing the activity of sulfinic acids.

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

2016-03-03
Minghao Feng , Bingqing Tang , Steven H. Liang +1 more
The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and 
 The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and natural products. For centuries, sulfur continues to maintain its status as the dominating heteroatom integrated into a set of 362 sulfur-containing FDA approved drugs (besides oxygen or nitrogen) through the present. Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades. In this review, these four moieties in pharmaceuticals and recent advances in the synthesis of the corresponding core scaffolds are presented. Keywords: Sulfur containing drugs, Sulfonamide, Thioether, Sulfones, Sulfur dioxide fixation, Organic synthesis
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Sulfur and Its Role In Modern Materials Science

2016-11-08
Darryl A. Boyd
Abstract Although well‐known and studied for centuries, sulfur continues to be at the center of an extensive array of scientific research topics. As one of the most abundant elements in 
 Abstract Although well‐known and studied for centuries, sulfur continues to be at the center of an extensive array of scientific research topics. As one of the most abundant elements in the Universe, a major by‐product of oil refinery processes, and as a common reaction site within biological systems, research involving sulfur is both broad in scope and incredibly important to our daily lives. Indeed, there has been renewed interest in sulfur‐based reactions in just the past ten years. Sulfur research spans the spectrum of topics within the physical sciences including research on improving energy efficiency, environmentally friendly uses for oil refinery waste products, development of polymers with unique optical and mechanical properties, and materials produced for biological applications. This Review focuses on some of the latest exciting ways in which sulfur and sulfur‐based reactions are being utilized to produce materials for application in energy, environmental, and other practical areas.

Visible-Light-Promoted C–S Cross-Coupling via Intermolecular Charge Transfer

2017-09-14
Bin Liu , Chern‐Hooi Lim , Garret M. Miyake
Disclosed is a mild, scalable, visible-light-promoted cross-coupling reaction between thiols and aryl halides for the construction of C–S bonds in the absence of both transition metal and photoredox catalysts. The 
 Disclosed is a mild, scalable, visible-light-promoted cross-coupling reaction between thiols and aryl halides for the construction of C–S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore, to demonstrate its utility, this C–S coupling protocol was applied in drug synthesis and late-stage modifications of active pharmaceutical ingredients. UV–vis spectroscopy and time-dependent density functional theory calculations suggest that visible-light-promoted intermolecular charge transfer within the thiolate–aryl halide electron donor–acceptor complex permits the reactivity in the absence of catalyst.
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Analysis of US FDA-Approved Drugs Containing Sulfur Atoms

2018-01-22
Kevin A. Scott , JĂłn T. Njardarson

A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor–Acceptor Cyanoarenes

2018-10-02
Elisabeth Speckmeier , Tillmann G. Fischer , Kirsten Zeitler
The targeted choice of specific photocatalysts has been shown to play a critical role for the successful realization of challenging photoredox catalytic transformations. Herein, we demonstrate the successful implementation of 
 The targeted choice of specific photocatalysts has been shown to play a critical role for the successful realization of challenging photoredox catalytic transformations. Herein, we demonstrate the successful implementation of a rational design strategy for a series of deliberate structural manipulations of cyanoarene-based, purely organic donor-acceptor photocatalysts, using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a starting point. Systematic modifications of both the donor substituents as well as the acceptors' molecular core allowed us to identify strongly oxidizing as well as strongly reducing catalysts (e.g., for an unprecedented detriflation of unactivated naphthol triflate), which additionally offer remarkably balanced redox potentials with predictable trends. Especially halogen arene core substitutions are instrumental for our targeted alterations of the catalysts' redox properties. Based on their preeminent electrochemical and photophysical characteristics, all novel, purely organic photoredox catalysts were evaluated in three challenging, mechanistically distinct classes of benchmark reactions (either requiring balanced, highly oxidizing or strongly reducing properties) to demonstrate their enormous potential as customizable photocatalysts, that outperform and complement prevailing typical best photocatalysts.

Pharmaceutical and medicinal significance of sulfur (SVI)-Containing motifs for drug discovery: A critical review

2018-11-22
Chuang Zhao , K.P. Rakesh , L. Ravidar +2 more
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Construction of sulfur-containing moieties in the total synthesis of natural products

2019-06-17
Nengzhong Wang , Puli Saidhareddy , Xuefeng Jiang
Covering: January 2013 to September 2018Sulfur-containing natural products are a large class of significant functional molecules. Many of these compounds exhibit potent biological activities and pharmacological properties; in fact, some 
 Covering: January 2013 to September 2018Sulfur-containing natural products are a large class of significant functional molecules. Many of these compounds exhibit potent biological activities and pharmacological properties; in fact, some of them have been developed into important drugs. The total synthesis of sulfur-containing natural products is a subject that has long attracted significant attention from synthetic organic chemists; to achieve this goal, various methods have been developed over the past years. This review surveys total syntheses of sulfur-containing natural products that introduce sulfur atoms using different sulfurization agents to construct related sulfur-containing moieties.

Synthetic Transformations of Vinyl and Aryl Triflates

1993-01-01
Kurt Ritter
The increasing use of vinyl and aryl trifluoromethanesulfonates (triflates) is due to their facile preparation from carbonyl compounds and phenols. They undergo cross-coupling reactions with organometallics as the corresponding organic 
 The increasing use of vinyl and aryl trifluoromethanesulfonates (triflates) is due to their facile preparation from carbonyl compounds and phenols. They undergo cross-coupling reactions with organometallics as the corresponding organic halides or addition reactions to alkenes and alkynes. Especially in the Heck reaction triflates proved to be superior to halides with respect to regio- and diastereoselectivity. Palladium-catalyzed carbon monoxide insertion of triflates leading to the corresponding esters or amides has found widespread application in natural product synthesis. Various deoxygenation procedures for ketones or phenols are based on the ease of removal of the trifluoromethanesulfoxy group. 1. Introduction 2. Synthesis of Vinyl and Aryl Triflates (Nonaflates, Fluorosulfonates) 3. Synthetic Transformations of Vinyl and Aryl Triflates 3.1. Carbon-Carbon Bond Formation 3.1.1. Cross-Coupling Reactions of Vinyl and Aryl Triflates with Organometallics 3.1.2. Cross-Coupling Reactions of Vinyl and Aryl Triflates with Alkenes, Alkynes, Allenes, Cyclopropanes and Ketene Silyl Acetals 3.1.3. Reactions of Vinyl and Aryl Triflates under CO Insertion 3.1.4. Reactions of Vinyl and Aryl Triflates with Cyanides 3.1.5. Reactions of Vinyl Triflates with Aldehydes (Nozaki-Hiyama Reaction) 3.1.6. Carbon-Carbon Bond Formation via Cationic Intermediates 3.2. Carbon-Tin Bond Formation 3.3. Carbon-Nitrogen Bond Formation 3.4. Carbon-Phosphorus Bond Formation 3.5. Carbon-Sulfur Bond Formation 3.6. Carbon-Halogen Bond Formation 3.7. Hydrogenation of Vinyl and Aryl Triflates or Nonaflates 3.8. Special Reactions 4. Conclusion Abbreviations: dba dibenzylidenacetone dppb bis(diphenylphosphino)butane dppp bis(diphenylphosphino)propane dppf diphenylphosphinoferrocene Bn benzyl TBDMS tert-butyldimethylsilyl Tf triflate Nf nonaflate

Renaissance of Ullmann and Goldberg Reactions - Progress in Copper Catalyzed C-N-, C-O- and C-S-Coupling

2003-01-01
K. Kunz , Ulrich Scholz , Dirk Ganzer
Copper-catalyzed C-N-, C-O- and C-S-coupling reactions are powerful tools in organic synthesis and have been extensively reinvestigated in the past five years. The understanding of solubilizing and accelerating effects exhibited 
 Copper-catalyzed C-N-, C-O- and C-S-coupling reactions are powerful tools in organic synthesis and have been extensively reinvestigated in the past five years. The understanding of solubilizing and accelerating effects exhibited by substrates and ligands initiated novel developments originally on N-arylation of amines, amides, and nitrogen heterocycles. Nevertheless practical methods for the syntheses of aryl ethers and aryl thioethers have been established as well. A wide range of arylating reagents was explored, of which the aryl halides will be presented in this overview. Among a growing set of ligands and optimized reaction protocols, the most promising procedures are highlighted, covering the literature published through May 2003.

A general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphines

2004-06-09
Miki Murata , Stephen L. Buchwald

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

2019-06-25
Daniel Kaiser , Immo Klose , Rik Oost +2 more
Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a 
 Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.
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Electrochemical Oxidative Cross-Coupling with Hydrogen Evolution Reactions

2019-11-27
Yong Yuan , Aiwen Lei
Oxidative cross-coupling has proved to be one of the most straightforward strategies for forming carbon-carbon and carbon-heteroatom bonds from easily available precursors. Over the past two decades, tremendous efforts have 
 Oxidative cross-coupling has proved to be one of the most straightforward strategies for forming carbon-carbon and carbon-heteroatom bonds from easily available precursors. Over the past two decades, tremendous efforts have been devoted in this field and significant advances have been achieved. However, in order to remove the surplus electrons from substrates for chemical bonds formation, stoichiometric oxidants are usually needed. Along with the development of modern sustainable chemistry, considerable efforts have been devoted to perform the oxidative cross-coupling reactions under external-oxidant-free conditions. Electrochemical synthesis is a powerful and environmentally benign approach, which can not only achieve the oxidative cross-couplings under external-oxidant-free conditions, but also release valuable hydrogen gas during the chemical bond formation. Recently, the electrochemical oxidative cross-coupling with hydrogen evolution reactions has been significantly explored. This Account presents our recent efforts toward the development of electrochemical oxidative cross-coupling with hydrogen evolution reactions. (1) We explored the oxidative cross-coupling of thiols/thiophenols with arenes, heteroarenes, and alkenes for C-S bond formation. (2) Using the strategy of electrochemical oxidative C-H/N-H cross-coupling with hydrogen evolution, we successfully realized the C-H amination of phenols, anilines, imidazopyridines, and even ethers. (3) Employing halide salts as the green halogenating reagents, we developed a clean C-H halogenation protocol under electrochemical oxidation conditions. To address the limitation that this reaction had to carry out in aqueous solvent, we also developed an alternative method that uses CBr4, CHBr3, CH2Br2, CCl3Br, and CCl4 as halogenating reagents and the mixture of acetonitrile and methanol as cosolvent. (4) We also developed an approach for constructing C-O bonds in a well-developed electrochemical oxidative cross-coupling with hydrogen evolution manner. (5) Under mild external-oxidant-free electrochemical conditions, we realized the C(sp2)-H and C(sp3)-H phosphonylation with modest to high yields. (6) We successfully achieved the S-H/S-H cross-coupling with hydrogen evolution under electrochemical oxidation conditions. By anodic oxidation instead of chemical oxidants, the overoxidation of thiols and thiophenols was well avoided. (7) The methods for constructing structurally diverse heterocyclic compounds were also developed via the electrochemical oxidative annulations. (8) We have also applied the electrochemical oxidative cross-coupling with hydrogen evolution strategy to the alkenes difunctionalization for constructing multiple bonds in one step, such as C-S/C-O bonds, C-S/C-N bonds, C-Se/C-O bonds, and C-Se/C-N bonds. We hope our studies will stimulate the research interest of chemists and pave the way for the discovery of more electrochemical oxidative cross-coupling with hydrogen evolution reactions.

Enantioselective Organocatalyzed α Sulfenylation of Aldehydes

2005-01-18
Mauro Marigo , Tobias C. Wabnitz , Doris Fielenbach +1 more
Leicht erhĂ€ltlich sind chirale α-sulfanylsubstituierte Aldehyde durch direkte Synthese aus unmodifizierten Aldehyden und 1-Benzylsulfanyl-1,2,4-triazol. Die Aldehyde werden in Gegenwart von sterisch anspruchsvollen chiralen Pyrrolidinderivaten als Organokatalysatoren mit hervorragenden EnantioselektivitĂ€ten erhalten 
 Leicht erhĂ€ltlich sind chirale α-sulfanylsubstituierte Aldehyde durch direkte Synthese aus unmodifizierten Aldehyden und 1-Benzylsulfanyl-1,2,4-triazol. Die Aldehyde werden in Gegenwart von sterisch anspruchsvollen chiralen Pyrrolidinderivaten als Organokatalysatoren mit hervorragenden EnantioselektivitĂ€ten erhalten (siehe Schema). R, Râ€Č=H, Alkyl, Allyl, Benzyl, Ph. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2005/z462101_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Sulphones in Organic Synthesis

1993-01-01
N. S. Simpkins

One-Pot Three-Component Cascade Strategy for the Site-Selective Synthesis of 5-Sulfenylated/Selenylated 2,4-Disubstituted Pyrimidines

2025-06-25
Zhiying Zhang , Yatang Wang , Xiaofeng Hua +6 more | Organic Letters
We describe an efficient synthesis of 5-sulfenylated/selenylated 2,4-disubstituted pyrimidines through the three-component cascade reaction of readily available enaminones, amidines, and thio/seleno-benzenesulfonates. This reaction simultaneously constructs two C-N bonds and one 
 We describe an efficient synthesis of 5-sulfenylated/selenylated 2,4-disubstituted pyrimidines through the three-component cascade reaction of readily available enaminones, amidines, and thio/seleno-benzenesulfonates. This reaction simultaneously constructs two C-N bonds and one C-S/Se bond through a one-pot method without the need for any external catalysts, metals, oxidants, or bases. This protocol features good functional group tolerance, a broad substrate scope, a simple operation procedure, high site selectivity, and a green reaction process. The utility of this strategy is demonstrated by gram-scale experiments and late-stage structural modifications of structurally complex molecules. Mechanistic studies indicate that the reaction begins with the enaminones attacking the sulfur atom of the thiophenyl sulfonates, followed by intermolecular cyclization with benzamidines to yield 5-sulfenylated 2,4-disubstituted pyrimidines.

CuF<sub>2</sub>-Catalyzed Chan–Lam Reaction of Saccharin: Solvent-Controlled Chemodivergent Synthesis of <i>N</i>-Arylsaccharin and Methyl 2-(<i>N</i>-Arylsulfamoyl)benzoates

2025-06-25
Tanumay Roy , S. Jana , Parthasarathi Das | The Journal of Organic Chemistry
A solvent-controlled CuF2-catalyzed Chan-Lam coupling of saccharin with arylboronic acids is reported, enabling the chemodivergent synthesis of N-arylsaccharin derivatives in dichloroethane and methyl 2-(N-arylsulfamoyl)benzoates in MeOH. A saccharin-DMAP zwitterion complex 
 A solvent-controlled CuF2-catalyzed Chan-Lam coupling of saccharin with arylboronic acids is reported, enabling the chemodivergent synthesis of N-arylsaccharin derivatives in dichloroethane and methyl 2-(N-arylsulfamoyl)benzoates in MeOH. A saccharin-DMAP zwitterion complex was isolated, which provided crucial mechanistic insights for the product distribution. This chemodivergent synthesis transformed saccharin into versatile synthons for the synthesis of a tianeptine analogue and an endothelin antagonist analogue, highlighting its pharmaceutical relevance.

Green‐Light Photocatalytic Synthesis of Non‐Proteinogenic Isothiocyanate‐Decorated Amino Acids from Lysine Residues and Carbon Disulfide

2025-06-25
Jingjie Hai , Hongyao Li , Yang Li +1 more | Advanced Synthesis & Catalysis
A sustainable and mild approach for the synthesis of nonproteinogenic isothiocyanate‐decorated amino acids from lysine residues and carbon disulfide via green‐light photocatalysis is described. A series of pharmacologically interesting isothiocyanate‐containing 
 A sustainable and mild approach for the synthesis of nonproteinogenic isothiocyanate‐decorated amino acids from lysine residues and carbon disulfide via green‐light photocatalysis is described. A series of pharmacologically interesting isothiocyanate‐containing amino acids and oligopeptides are synthesized for the first time through the desulfurization method with the wide tolerance of protected groups and amino acid residues. The produced unnatural amino acids can be successfully converted into thioamide‐containing amino acids such as thiocitrulline and its analogs. Mechanism studies support the dithiocarbamate radical coupling, deprotonation, and desulfurization processes. This approach expands the scope of nonproteinogenic amino acids and provides a new type of amino acid residues with a robust active site, which are significant organic building blocks and potential biological diagnostic markers.

Radical Cross-Coupling Reaction of NPIB Ester with Sodium Sulfinate Salts for the Synthesis of Sulfones

2025-06-25
Syed Anis Ali Shah , Bo-Xi Liu , Muhammad Hasan +5 more | The Journal of Organic Chemistry
Herein, we report decarboxylative sulfonylation involving α-N-phthalimido-oxy isobutyrate (NPIB) as a radical precursor. We successfully developed different NPIBs from N-hydroxyphthalimide and alkyl butyl isobutyrate and subjected them to reactions with 
 Herein, we report decarboxylative sulfonylation involving α-N-phthalimido-oxy isobutyrate (NPIB) as a radical precursor. We successfully developed different NPIBs from N-hydroxyphthalimide and alkyl butyl isobutyrate and subjected them to reactions with easily available sodium sulfinate salts as the sulfonylating source. A successful reaction was executed using Cu/4-CzIPN as dual catalysts under blue LED irradiation. The reaction featured functional group tolerance, compatibility with a wide range of sodium sulfinate salts, easily accessible starting materials, and moderate reaction conditions.

Overcoming Challenges in Small‐Ring Transfer: Direct Decarboxylative Hydroalkylation of Alkenes via Iron‐Thiol Catalysis

2025-06-24
Rahul Giri , Po-Kai Peng , Anthony J. Fernandes +3 more | Angewandte Chemie International Edition
Cyclopropanes, especially those substituted with trifluoromethyl (CF3) groups, are valuable scaffolds in medicinal chemistry. Their enhanced bioavailability contributes to the widespread presence of this motif in a variety of bioactive 
 Cyclopropanes, especially those substituted with trifluoromethyl (CF3) groups, are valuable scaffolds in medicinal chemistry. Their enhanced bioavailability contributes to the widespread presence of this motif in a variety of bioactive compounds. Despite the development of multiple synthetic strategies, a direct method for transferring CF3‐containing small rings from their most abundant carboxylic acid surrogates remains a significant challenge. In this work, we overcome the challenging decarboxylation of CF3‐cyclopropyl and CF3‐cyclobutyl carboxylic acids while leveraging the ligand‐to‐metal charge transfer (LMCT) excited state of photochemically activated iron complexes. The resulting radicals were then engaged in radical addition to alkenes, followed by a timely hydrogen atom transfer (HAT) process mediated by a thiol donor. This efficient iron‐thiol cooperative catalysis enables, for the first time, facile hydroalkylation of alkenes with highly reactive CF3‐containing cyclopropyl and cyclobutyl radicals. Synergistic experimental, spectroscopic, and density functional theory (DFT) studies support the proposed reaction mechanism. Additionally, we employed the radical stabilization energy (RSE) scale, developed using isodesmic equations computed at the DFT level, aiming to provide a better understanding of the reluctant radical decarboxylation of small‐strained cycloalkanes.

Zinc‐Promoted Synthesis of ÎČ‐(Thio)uredo‐Sulfides from Isothiocyanates and Tertiary Amines

2025-06-24
Pankaj Kumar , Jaswinder Kaur , Aman Bhalla | Chemistry - An Asian Journal
Herein, we highlight the sequential Zn-promoted reactivity of isothiocyanates towards tertiary aliphatic amines with subsequent regioselective N-dealkylation, yielding respective thioureas. Under non-inert conditions Zn functions as a desulfurizing agent affording 
 Herein, we highlight the sequential Zn-promoted reactivity of isothiocyanates towards tertiary aliphatic amines with subsequent regioselective N-dealkylation, yielding respective thioureas. Under non-inert conditions Zn functions as a desulfurizing agent affording ZnS, while water acts as an oxygen source, facilitating the direct transformation of isothiocyanates into ureas. This strategy affords b-(thio)uredo-sulphides, important functionalities in synthetic and biological important functionalities. Through a comprehensive examination of the mechanism and substrate scope, we elucidate a non-radical pathway with Hofmann elimination as initial and desulfurization as final steps.

Visible-Light-Induced Direct C(sp<sup>3</sup>)–H Phosphorylation through Radical Cross-Coupling by Polyoxomolybdate Photocatalyst

2025-06-24
Ye Li , Qiaoyu Gan , Xiaosong Wang +4 more | ACS Sustainable Chemistry & Engineering

Overcoming Challenges in Small‐Ring Transfer: Direct Decarboxylative Hydroalkylation of Alkenes via Iron‐Thiol Catalysis

2025-06-24
Rahul Giri , Po-Kai Peng , Anthony J. Fernandes +3 more | Angewandte Chemie
Cyclopropanes, especially those substituted with trifluoromethyl (CF3) groups, are valuable scaffolds in medicinal chemistry. Their enhanced bioavailability contributes to the widespread presence of this motif in a variety of bioactive 
 Cyclopropanes, especially those substituted with trifluoromethyl (CF3) groups, are valuable scaffolds in medicinal chemistry. Their enhanced bioavailability contributes to the widespread presence of this motif in a variety of bioactive compounds. Despite the development of multiple synthetic strategies, a direct method for transferring CF3‐containing small rings from their most abundant carboxylic acid surrogates remains a significant challenge. In this work, we overcome the challenging decarboxylation of CF3‐cyclopropyl and CF3‐cyclobutyl carboxylic acids while leveraging the ligand‐to‐metal charge transfer (LMCT) excited state of photochemically activated iron complexes. The resulting radicals were then engaged in radical addition to alkenes, followed by a timely hydrogen atom transfer (HAT) process mediated by a thiol donor. This efficient iron‐thiol cooperative catalysis enables, for the first time, facile hydroalkylation of alkenes with highly reactive CF3‐containing cyclopropyl and cyclobutyl radicals. Synergistic experimental, spectroscopic, and density functional theory (DFT) studies support the proposed reaction mechanism. Additionally, we employed the radical stabilization energy (RSE) scale, developed using isodesmic equations computed at the DFT level, aiming to provide a better understanding of the reluctant radical decarboxylation of small‐strained cycloalkanes.

Allenyl Sulfones as Substrates in [4+2] Annulation to Access Thiochroman-4-ols

2025-06-23
| Synfacts

Iminothiolation of Alkenes by Metal-Free Photocatalytic Energy Transfer

2025-06-23
| Synfacts

Photoinduced Nickel-Catalyzed 1,2-Acylcyanation of Styrenes with Acyl Fluorides and Trimethylsilyl Cyanide

2025-06-23
| Synfacts

Magnetite-Catalyzed Cross-Dehydrogenative Coupling of Aldehydes and Thiols Forming Thioesters

2025-06-23
| Synfacts

Asymmetric Counteranion Directed Photoredox Catalysis (ACPC)-Enabled Deracemization of Ketones

2025-06-23
| Synfacts

Regioselective Sulfenylation/Phosphorylation of Unactivated Alkenes via Thianthrenation

2025-06-23
Jing Xiao , Lude Wang , Mengfan Wang +4 more | Organic Letters
We report the first successful realization of sulfenylation/phosphorylation of unactivated alkenes via thianthrenation. This strategy achieves regioselective C-S/C-P bond formation in one pot by reacting alkenylsulfonium salts with diaryl disulfides 
 We report the first successful realization of sulfenylation/phosphorylation of unactivated alkenes via thianthrenation. This strategy achieves regioselective C-S/C-P bond formation in one pot by reacting alkenylsulfonium salts with diaryl disulfides and P(O)-H reagents under basic conditions. The transition-metal- and catalyst-free protocol features mild reaction conditions and broad substrate compatibility, affording a new approach for the selective construction of sulfur- and phosphorus-embedded molecular architectures.

Photocatalyst-Dependent Deracemization of Cyclic α-Aryl Ketones via ACPC

2025-06-23
| Synfacts

Radical‐Mediated Sulfonylarylation of Unactivated Alkynes via Intramolecular 1,4‐(hetero)aryl Migration

2025-06-23
Xu Zhang , Fushan Chen , Chen Zhu | ChemistryEurope
Radical‐mediated difunctionalization of alkynes is an extensively explored strategy for diverse alkyne transformation and utilization. However, the direct difunctionalization of unactivated alkynes remains a significant challenge. In this study, a 
 Radical‐mediated difunctionalization of alkynes is an extensively explored strategy for diverse alkyne transformation and utilization. However, the direct difunctionalization of unactivated alkynes remains a significant challenge. In this study, a novel visible light‐induced, redox‐neutral sulfonylarylation of unactivated alkynes is reported, facilitated by a radical‐mediated intramolecular 1,4‐(hetero)aryl migration. Notably, this transformation enables the synthesis of a diverse array of multisubstituted vinyl sulfones, with tunable ( E )‐ and ( Z )‐selectivity controlled by the wavelength of visible light. This method features mild reaction conditions, excellent regio‐ and stereoselectivity, and broad functional group compatibility.

Sustainable Synthesis of Diverse 1,1-Aminosilane Libraries Using a Multicomponent Cu-Catalyzed Reaction

2025-06-23
Lissett Barrios , M Castro Manzanares , Melissa Zamora +1 more | Organic Letters
Herein, we report a high-yielding, cost-effective, operationally simple, and readily scalable Cu-catalyzed multicomponent reaction for the synthesis of 1,1-aminosilanes from feedstock amine and aldehyde reagents. This method is compatible with 
 Herein, we report a high-yielding, cost-effective, operationally simple, and readily scalable Cu-catalyzed multicomponent reaction for the synthesis of 1,1-aminosilanes from feedstock amine and aldehyde reagents. This method is compatible with aliphatic, aromatic, and heteroaromatic aldehydes and primary and secondary amines and is adaptable to the late-stage modification of FDA approved drugs and their direct precursors. Additionally, this method benefits from low catalyst loadings, mild reaction conditions, equimolar reagent concentrations, and the synthesis of air-stable products.

Catalyst-Controlled Cycloaddition for the Synthesis of Bridged Sulfur Heterocycles

2025-06-23
| Synfacts

Metal Chloride-Functionalized Ionic Liquids for Highly Efficient H<sub><b>2</b></sub>S Conversion into Value-Added Elemental Sulfur: A Comprehensive Optimization Study and Techno-Economic Analysis

2025-06-22
Muhammad Syahir Aminuddin , Mohamad Azmi Bustam , Chong Yang Chuah +1 more | Industrial & Engineering Chemistry Research

Visible Light‐Driven Deracemization of Cyclic Sulfonamides by Quinuclidine and Chiral Arylthiol Catalysis

2025-06-21
Lei Dai , Jing Wang , Chaoren Shen +2 more | Angewandte Chemie
A photocatalytic system comprising an achiral tertiary amine and a chiral C2‐symmetric arylthiol was developed for the deracemization of various cyclic sulfonamides. This protocol exhibited high yields, good to excellent 
 A photocatalytic system comprising an achiral tertiary amine and a chiral C2‐symmetric arylthiol was developed for the deracemization of various cyclic sulfonamides. This protocol exhibited high yields, good to excellent enantioselectivity, and broad substrate scope. The resulting products can be readily transformed into diverse diarylmethylamines, presenting a viable alternative to metal‐catalyzed asymmetric methods. The reaction pathway involving a relay of non‐enantioselective hydrogen‐atom abstraction (HAA) and enantioselective hydrogen‐atom delivery (HAD).

Microwave‐Assisted Metal‐Free Synthesis of Vinyl Sulfoxides Using DMSO as Solvent and Reagent

2025-06-21
Desai Bhavyesh , Arti Ramani , Monak Patel +4 more | Asian Journal of Organic Chemistry
Abstract Among organosulfur compounds, sulfoxides play a crucial role in many biologically active substances with a diverse range of applications in natural products, pharmaceuticals, agrochemicals, and materials. We have developed 
 Abstract Among organosulfur compounds, sulfoxides play a crucial role in many biologically active substances with a diverse range of applications in natural products, pharmaceuticals, agrochemicals, and materials. We have developed an efficient microwave‐assisted method for synthesizing vinyl sulfoxides through oxidative condensation of easily accessible aromatic aldehydes or benzyl alcohols with dimethyl sulfoxide (DMSO), using a base under ambient conditions. In this method, DMSO serves a dual purpose: it acts as a source of the (methylsulfinyl)methyl group (─CH₂SOMe) and functions as a solvent. This protocol is highly tolerant of various aromatic aldehydes, including heteroaryl and α,ÎČ‐unsaturated aldehydes, yielding corresponding vinyl sulfoxides in good to excellent yields. Additionally, this methodology can also be applied to synthesize various vinyl sulfoxides from benzyl alcohols, yielding moderate to good results. The advantages of this strategy include being metal‐free, requiring short reaction times, maintaining mild conditions, operational simplicity, high selectivity, and achieving moderate to excellent yields.

Electrocatalytic C–S Cross‐Coupling via Engineered Frustrated Lewis Acid‐Base Pairs for High‐Efficiency Methanesulfonate Synthesis

2025-06-21
Yuhang Gao , Menglong Sun , Jing Yuan +7 more | Angewandte Chemie International Edition
The electrochemical synthesis of sulfonyl compounds under mild conditions remains a significant challenge due to the reliance on harsh reagents, high energy consumption, and low selectivity in conventional methods. Herein, 
 The electrochemical synthesis of sulfonyl compounds under mild conditions remains a significant challenge due to the reliance on harsh reagents, high energy consumption, and low selectivity in conventional methods. Herein, we report a novel strategy for efficient C–S bond formation through in situ modulation of frustrated Lewis acid‐base pairs within a copper‐based metal‐organic framework (CuBDC‐XN). By precisely engineering electron‐deficient Cu Lewis acid sites and electron‐rich XN‐functionalized Lewis base sites, this bifunctional catalyst enables the synergistic co‐reduction of SO32‐ and CO2 into methanesulfonate (MS) at ambient conditions with a Faradaic efficiency of 13.77% (−0.78 V vs. RHE). Mechanistic studies reveal that the frustrated Lewis pairs selectively stabilize key intermediates (*CHO and SO32‐) via electrostatic interactions, facilitating nucleophilic attack and C–S coupling with a reduced energy barrier (0.48 eV). In situ spectroscopic analyses and DFT calculations further elucidate the dynamic adsorption‐configuration regulation and intermediate evolution pathway. This work not only establishes a molecular‐level understanding of cooperative Lewis acid‐base catalysis but also provides a universal design principle for the sustainable electrosynthesis of value‐added organosulfur compounds.

Electrocatalytic C–S Cross‐Coupling via Engineered Frustrated Lewis Acid‐Base Pairs for High‐Efficiency Methanesulfonate Synthesis

2025-06-21
Yuhang Gao , Menglong Sun , Jing Yuan +7 more | Angewandte Chemie
The electrochemical synthesis of sulfonyl compounds under mild conditions remains a significant challenge due to the reliance on harsh reagents, high energy consumption, and low selectivity in conventional methods. Herein, 
 The electrochemical synthesis of sulfonyl compounds under mild conditions remains a significant challenge due to the reliance on harsh reagents, high energy consumption, and low selectivity in conventional methods. Herein, we report a novel strategy for efficient C–S bond formation through in situ modulation of frustrated Lewis acid‐base pairs within a copper‐based metal‐organic framework (CuBDC‐XN). By precisely engineering electron‐deficient Cu Lewis acid sites and electron‐rich XN‐functionalized Lewis base sites, this bifunctional catalyst enables the synergistic co‐reduction of SO32‐ and CO2 into methanesulfonate (MS) at ambient conditions with a Faradaic efficiency of 13.77% (−0.78 V vs. RHE). Mechanistic studies reveal that the frustrated Lewis pairs selectively stabilize key intermediates (*CHO and SO32‐) via electrostatic interactions, facilitating nucleophilic attack and C–S coupling with a reduced energy barrier (0.48 eV). In situ spectroscopic analyses and DFT calculations further elucidate the dynamic adsorption‐configuration regulation and intermediate evolution pathway. This work not only establishes a molecular‐level understanding of cooperative Lewis acid‐base catalysis but also provides a universal design principle for the sustainable electrosynthesis of value‐added organosulfur compounds.

Visible Light‐Driven Deracemization of Cyclic Sulfonamides by Quinuclidine and Chiral Arylthiol Catalysis

2025-06-21
Lei Dai , Jing Wang , Chaoren Shen +2 more | Angewandte Chemie International Edition
A photocatalytic system comprising an achiral tertiary amine and a chiral C2‐symmetric arylthiol was developed for the deracemization of various cyclic sulfonamides. This protocol exhibited high yields, good to excellent 
 A photocatalytic system comprising an achiral tertiary amine and a chiral C2‐symmetric arylthiol was developed for the deracemization of various cyclic sulfonamides. This protocol exhibited high yields, good to excellent enantioselectivity, and broad substrate scope. The resulting products can be readily transformed into diverse diarylmethylamines, presenting a viable alternative to metal‐catalyzed asymmetric methods. The reaction pathway involving a relay of non‐enantioselective hydrogen‐atom abstraction (HAA) and enantioselective hydrogen‐atom delivery (HAD).

Thiolate-Initiated Metal-Free Synthesis of Cyclopentenones via a Halogen-Stabilized Vinyl Carbanion

2025-06-20
Lea Sophie Umlauf , Christoph Wölper , Gebhard Haberhauer | Synlett
A metal-free synthesis of cyclopentenones is described. The mechanism proceeds via a halogen-stabilized carbanion generated by the nucleophilic attack of a thiolate on a haloalkyne moiety. The sp2-hybridized carbanion undergoes 
 A metal-free synthesis of cyclopentenones is described. The mechanism proceeds via a halogen-stabilized carbanion generated by the nucleophilic attack of a thiolate on a haloalkyne moiety. The sp2-hybridized carbanion undergoes cyclization to an embedded ester carbonyl, yielding the cyclopentenone. The reaction exhibits a broad tolerance toward functional groups and proceeds under mild conditions.

Accessing sulfonamides via formal SO2 insertion into C–N bonds

2025-06-20
Myojeong Kim , Carys E Obertone , Christopher B. Kelly +4 more | Nature Chemistry

Construction of C‒S Bond via Reductive Cross-Coupling

2025-06-18
Muhammad Bilal , Xiaobo Liu , Yu‐Feng Liang | Tetrahedron Chem

Visible-Light-Driven Photocatalytic Synthesis of Polysubstituted Pyrrolidines via Desulfurative Tandem Cyclization of Thiols with 1,6-Enynes

2025-06-18
Hongda Xia , H. B. Yang , Jiangna Yue +3 more | The Journal of Organic Chemistry
A metal-free visible-light photoredox-catalyzed tandem cyclization of 1,6-enynes with thiols was successfully developed. This method provides efficient access to a wide range of five-membered heterocyclic compounds in good to excellent 
 A metal-free visible-light photoredox-catalyzed tandem cyclization of 1,6-enynes with thiols was successfully developed. This method provides efficient access to a wide range of five-membered heterocyclic compounds in good to excellent yields with high regioselectivity through a desulfurative/cyclization/HAT process. The versatility of this reaction is demonstrated by its compatibility with a variety of N-tethered 1,6-enynes, encompassing diverse electronic and steric properties. Notably, the cascade reaction demonstrates remarkable operational simplicity, high bond-forming efficiency, and potential scalability, as exemplified by its successful implementation in gram-scale synthesis, which is expected to have potential applications in organic synthesis.

Triplet Ketone Catalysis-Enabled Functionalization of Thioanisoles with Maleimides

2025-06-18
Akash Bisoyi , Ramsiya Poolamanna , Alisha Rani Tripathy +1 more | The Journal of Organic Chemistry
Considering the importance of sulfur-containing organic molecules in various domains of chemistry, we report herein a protocol for the catalytic diastereoselective synthesis of tricyclic heterocycles through α-C(sp3)-H functionalization of thioanisoles 
 Considering the importance of sulfur-containing organic molecules in various domains of chemistry, we report herein a protocol for the catalytic diastereoselective synthesis of tricyclic heterocycles through α-C(sp3)-H functionalization of thioanisoles with maleimides enabled by triplet ketone catalysis. Mild reaction conditions, an inexpensive photocatalyst, molecular oxygen as a terminal oxidant, and compatibility with various functional groups are advantages of the protocol. Preliminary mechanistic studies suggest the generation of α-thioalkyl radicals and involvement of aerial oxygen in our reaction conditions.

Photocatalytic Redox-Neutral Alkoxysulfonylation of Alkenes

2025-06-18
Jie Gong , Fang Wang , Yan‐Biao Kang +1 more | The Journal of Organic Chemistry
ÎČ-Alkoxy sulfones are important building blocks in organic synthesis. Herein, we report that CBZ6 is an efficient redox-neutral photocatalyst for the highly effective alkoxysulfonylation of alkenes with sulfonyl chlorides. This 
 ÎČ-Alkoxy sulfones are important building blocks in organic synthesis. Herein, we report that CBZ6 is an efficient redox-neutral photocatalyst for the highly effective alkoxysulfonylation of alkenes with sulfonyl chlorides. This process is enabled by the addition of a sulfonyl radical to an alkene to generate the benzyl radical. The following oxidation of the benzyl radical leads to the benzyl cationic intermediate, which is then captured by alkoxy anions.

Electrochemically Driven Hydroxy‐Thiocarbamation of Electron‐Deficient Alkenes

2025-06-17
Yu‐Fang Tan , Lan‐Xi Zong , Zhi Guan +1 more | Advanced Synthesis & Catalysis
This article reports the first example of multi‐component hydroxy‐thiocarbamation of electron‐deficient alkenes in an electrochemical undivided cell. Simple and readily available electron‐deficient (hetero)aryl alkenes, KSCN and H 2 O are 
 This article reports the first example of multi‐component hydroxy‐thiocarbamation of electron‐deficient alkenes in an electrochemical undivided cell. Simple and readily available electron‐deficient (hetero)aryl alkenes, KSCN and H 2 O are used as starting materials to produce ÎČ‐hydroxy primary S‐thiocarbamate derivatives in moderate to good yields. H 2 O is involved in the formation of carbamoyl and hydroxyl groups, making the method highly atom‐economical. The reaction introduces multiple functional groups under mild and environmentally friendly conditions, without the need for metals or external oxidants. The reaction exhibits good functional‐group tolerance and excellent product diversity. The procedure is operationally simple, and late‐stage modification of natural products further demonstrates the practical application of the method.

Organophotocatalyzed Radical Hydrophosphonylation of Acrylates, α,ÎČ-Unsaturated Ketones, Coumarins, Quinoxalinones, and <i>p</i>-Quinone Methides

2025-06-17
Nisha Rawat , Parashuram Sharma , Seshadri Reddy Nasireddy +2 more | The Journal of Organic Chemistry
An efficient and general organophotocatalytic protocol for the hydrophosphonylation of electron-deficient alkenes is reported. Thioxanthone catalyzed generation of phosphonyl radicals from H-phosphine oxides enabled expeditious access to a range of 
 An efficient and general organophotocatalytic protocol for the hydrophosphonylation of electron-deficient alkenes is reported. Thioxanthone catalyzed generation of phosphonyl radicals from H-phosphine oxides enabled expeditious access to a range of ÎČ-phosphonylated esters, ketones, nitriles, amides, and Îł-ketophosphine oxides, in excellent yields. This protocol features simple operating conditions, proceeds under mild conditions, provides access to an impressive array of diverse structural scaffolds, and exhibits broad functional group tolerance.

Photoinduced Aminosulfonylation of Unactivated Alkenes via N–N Bond Cleavage and Distal Migration of Imine

2025-06-16
Xin Liu , Longyu Wang , Muliang Zhang +1 more | Organic Letters
Given the crucial role of ÎČ-amino sulfones in the synthesis of functional materials and drug development, an efficient and straightforward synthetic protocol for accessing them is highly desirable. Herein, we 
 Given the crucial role of ÎČ-amino sulfones in the synthesis of functional materials and drug development, an efficient and straightforward synthetic protocol for accessing them is highly desirable. Herein, we present a novel strategy for achieving aminosulfonylation of unactivated alkenes via photoinduced N-N bond cleavage and imine distal migration. This method is metal-free, exhibits high atom economy, and demonstrates good functional group tolerance, offering a simple, green, and broadly applicable approach for synthesizing ÎČ-amino sulfone derivatives.

SYNTHESIS OF SULFUR-CONTAINING COMPOUNDS WITH THE PARTICIPATION OF ORGANOMETALLIC REAGENTS

2025-06-16
В. Đ . ĐŃ…ĐŒĐ”Ń‚ĐŸĐČĐ° | Izvestia Ufimskogo Nauchnogo Tsentra RAN
The aim of the study is to demonstrate the synthetic potential of organometallic compounds in the synthesis of acyclic and cyclic sulfur-containing compounds, which are characterized by wide practical application. 
 The aim of the study is to demonstrate the synthetic potential of organometallic compounds in the synthesis of acyclic and cyclic sulfur-containing compounds, which are characterized by wide practical application. Particular interest in sulfur compounds is primarily due to their use as inhibitors of the development of pathogenic microorganisms – viruses, bacteria, fungi, which are capable of mutating and developing resistance to the drugs used. In this regard, a wide arsenal of biologically active S-containing compounds is needed. An analysis of studies in the field of S-functionalization of halogen derivatives, thiones, unsaturated compounds under the action of organometallic reagents is carried out, and studies of the Ufa school of chemists, namely the scientific group of Professor A.G. Ibragimov, in which methods of synthesis of sulfur-containing compounds under the action of metal complex catalysis were actively studied

Photoinduced iron-catalyzed direct coupling of cycloalkanes and <i>N</i>-sulfonyl ketimines using air as oxidant

2025-06-16
Zihao Xia , Wenhao Liu , Xiaoyun Sun +3 more | Chemical Synthesis
An iron-catalyzed direct coupling of cycloalkanes and N -sulfonyl ketimines enabled by photoinduced ligand-to-metal charge transfer (LMCT) and energy transfer has been developed. This reaction demonstrates high atom economy and 
 An iron-catalyzed direct coupling of cycloalkanes and N -sulfonyl ketimines enabled by photoinduced ligand-to-metal charge transfer (LMCT) and energy transfer has been developed. This reaction demonstrates high atom economy and operates under eco-friendly, mild conditions with a good substrate scope. A notable aspect of this study is the proposal of a potential radical-radical coupling mechanism, involving a cycloalkyl radical and a cation radical intermediate, which may lead to C–C bond formation. This discovery significantly enhances our comprehension of reaction mechanisms in this domain.

Aryl Thiocyanate as an Organic ‘CN’ Source: Access to Thiocyano‐Thioesters from Cyclic Thioacetals

2025-06-16
Mousumi Behera , Shubham Y. Shukla , Pankaj D. Dharpure +1 more | Chemistry - An Asian Journal
Abstract A facile, transition metal‐free method has been developed for the synthesis of thiocyano–thioesters. It employs cyclic thioacetals and aryl thiocyanate as an organic ‘CN’ source, facilitated by organophotocatalyst under 
 Abstract A facile, transition metal‐free method has been developed for the synthesis of thiocyano–thioesters. It employs cyclic thioacetals and aryl thiocyanate as an organic ‘CN’ source, facilitated by organophotocatalyst under the visible light irradiation. Additionally, the diaryl disulfide by‐products have been efficiently repurposed as a recyclable and reusable substrates for the sustainable synthesis of aryl thiocyanates, supporting the circular chemical economy. This method exhibits broad functional group tolerance and is applicable to five‐ to eight‐membered cyclic thioacetals. The method also proved to be scalable on gram quantity. A series of control experiments, fluorescence quenching, and cyclic voltammetry analysis supported the proposed reaction mechanism.

The sulfenylation of imidazopyridines with sulfinic acids mediated by DTBP/HCl

2025-06-16
Yu Wang , Hongkun Huang , Xueyu Fang +4 more | Results in Chemistry

Synthesis, Characterization and Biological Evaluation of a Sulfonamide-Based Antimicrobial Agent

2025-06-16
Aref Atefi , Mohaddeseh Larypoor , Masoumeh Tabatabaee +1 more | Chemistry Africa

Pyrazole-Sulfone hybridization via silver-catalyzed regioselective aza-Michael addition of pyrazoles to vinyl sulfones: Synthesis of <i>N</i> -sulfonylethylated pyrazoles

2025-06-13
Xue Zhang , Yang Song , Yu Peng +4 more | Synthetic Communications

One‐Pot Tandem Alkylsulfonylation/Cyclization of Unactivated Alkenes to Construct Alkylsulfonyl‐Containing Polycyclic Quinazolinones Under Photocatalysis

2025-06-13
Rong Huang , Zhen Yao , Jing Guan +6 more | Asian Journal of Organic Chemistry
Abstract Visible‐light photoredox‐catalyzed one‐pot tandem alkylsulfonylation/cyclization of unactivated alkenes to construct alkylsulfonyl‐containing polycyclic quinazolinones from 4‐alkyl Hantzsch esters, DABCO(SO 2 ) 2 and N‐alkene‐tethered quinazolinones has been accomplished. This mild 
 Abstract Visible‐light photoredox‐catalyzed one‐pot tandem alkylsulfonylation/cyclization of unactivated alkenes to construct alkylsulfonyl‐containing polycyclic quinazolinones from 4‐alkyl Hantzsch esters, DABCO(SO 2 ) 2 and N‐alkene‐tethered quinazolinones has been accomplished. This mild transformation accommodates diversely decorated substrates, affords the target products in 69–90% yields, and can be readily scaled up. The efficacy of the current catalysis arises from the use of tetrabutylammonium decatungstate as the photocatalyst and cheap K 2 S 2 O 8 as the oxidant.

Dual NHC/Organophotoredox-Catalyzed Radical Phosphinoylacylation of Alkenes with Acyl Fluorides and H-Phosphine Oxides

2025-06-12
Ruilin Yang , Jia-Bin Liao , Hui Xi +2 more | The Journal of Organic Chemistry
A dual NHC/photoredox-catalyzed radical phosphinoylacylation of alkenes has been developed with organic dye Eosin Y as organophotocatalyst under green light irradiation. In this reaction, readily available acyl fluorides and secondary 
 A dual NHC/photoredox-catalyzed radical phosphinoylacylation of alkenes has been developed with organic dye Eosin Y as organophotocatalyst under green light irradiation. In this reaction, readily available acyl fluorides and secondary phosphine oxides are used as radical precursors to simultaneously construct C-C and C-P bonds. A wide range of ÎČ-phosphinoyl ketones are smoothly accessed in moderate to good yields under these mild reaction conditions. The scale-up reaction and synthesis of new valuable organophosphorus compounds, such as phosphine-olefin ligands, highlight the great potential applications of this approach. In addition, the preliminary mechanistic studies support the generation of the phosphorus radical and ketyl radical.

Divergent Synthesis of 1,6-Dicarbonyls and Sulfone-Bridged 1,7-Dicarbonyls from <i>N</i>-(Arylsulfonyl)acrylamides and Cyclopropanols via the Control of SO<sub>2</sub> Insertion

2025-06-12
Fei Chen , Libang Feng , Anqi Zhao +7 more | The Journal of Organic Chemistry
Preparation of two or more different products with excellent chemoselectivity from the same set of readily available substrates is a fascinating and challenging synthesis strategy. Herein, we describe the divergent 
 Preparation of two or more different products with excellent chemoselectivity from the same set of readily available substrates is a fascinating and challenging synthesis strategy. Herein, we describe the divergent synthesis of 1,6-dicarbonyls and sulfone-bridged 1,7-dicarbonyls, which bear an α-all-carbon quaternary stereocenter, from N-(arylsulfonyl)acrylamides and cyclopropanols. This reaction went through a radical cascade cyclopropyl alcohol ring-opening/selective insertion or noninsertion of the SO2/Truce-Smiles rearrangement process. The success of late-stage functionalization of drug derivatives and gram-scale preparation demonstrates the practical application potential of this strategy in organic synthesis and drug discovery.