Chemistry › Organic Chemistry

Oxidative Organic Chemistry Reactions

Works Count: 58538

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Description

This cluster of papers focuses on the catalytic oxidation of alcohols, utilizing various catalyst systems including hypervalent iodine compounds, transition metal catalysts, and organocatalysts. The research emphasizes aerobic oxidation, selective oxidation, enantioselective synthesis, and the application of green chemistry principles.

Keywords

Alcohol Oxidation; Catalytic; Hypervalent Iodine Compounds; Aerobic Oxidation; Transition Metal Catalysts; Organocatalysts; Selective Oxidation; Enantioselective Synthesis; Green Chemistry; Homogeneous Catalysts

The Chemistry of Indoles

1970-01-01

Richard J. Sundberg

Diaryliodonium Salts: A Journey from Obscurity to Fame

2009-10-29

Eleanor A. Merritt , Berit Olofsson

The recent groundbreaking developments in the application of diaryliodonium salts in cross-coupling reactions has brought this class of previously underdeveloped reagents to the forefront of organic chemistry. With the advent … The recent groundbreaking developments in the application of diaryliodonium salts in cross-coupling reactions has brought this class of previously underdeveloped reagents to the forefront of organic chemistry. With the advent of novel, facile, and efficient synthetic routes to these compounds, many more applications can be foreseen. Herein we provide an overview of the historical and recent advances in the synthesis and applications of diaryliodonium salts.

A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds

1981-09-01

Per H. J. Carlsen , Tsutomu Katsuki , Victor S. Martı́n +1 more

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compoundsPer H. J. Carlsen, Tsutomu Katsuki, Victor S. Martin, and K. Barry SharplessCite this: J. Org. … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compoundsPer H. J. Carlsen, Tsutomu Katsuki, Victor S. Martin, and K. Barry SharplessCite this: J. Org. Chem. 1981, 46, 19, 3936–3938Publication Date (Print):September 1, 1981Publication History Published online1 May 2002Published inissue 1 September 1981https://pubs.acs.org/doi/10.1021/jo00332a045https://doi.org/10.1021/jo00332a045research-articleACS PublicationsRequest reuse permissionsArticle Views17252Altmetric-Citations1602LEARN 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 Get e-Alerts

A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds

1997-10-01

A. DE MICO , Roberto Margarita , Luca Parlanti +2 more

Catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) are used in combination with [bis(acetoxy)iodo]benzene (BAIB) as a stoichiometric oxidant in the conversion of primary and secondary alcohols to carbonyl compounds. This procedure works … Catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) are used in combination with [bis(acetoxy)iodo]benzene (BAIB) as a stoichiometric oxidant in the conversion of primary and secondary alcohols to carbonyl compounds. This procedure works efficiently at room temperature in almost all common solvents and neat in some cases. This process exhibits a very high degree of selectivity for the oxidation of primary alcohols to aldehydes, without any noticeable overoxidation to carboxyl compounds, and a high chemoselectivity in the presence of either secondary alcohols or of other oxidizable moieties. This procedure allows an easy, convenient, high-yielding method for the oxidation of alcohols starting from commercially available compounds.

A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species

1991-09-01

D. B. DESS , J. C. Martin

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 speciesDaniel B. Dess and J. … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 speciesDaniel B. Dess and J. C. MartinCite this: J. Am. Chem. Soc. 1991, 113, 19, 7277–7287Publication Date (Print):September 1, 1991Publication History Published online1 May 2002Published inissue 1 September 1991https://pubs.acs.org/doi/10.1021/ja00019a027https://doi.org/10.1021/ja00019a027research-articleACS PublicationsRequest reuse permissionsArticle Views23312Altmetric-Citations2093LEARN 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 Get e-Alerts

Highly Practical Copper(I)/TEMPO Catalyst System for Chemoselective Aerobic Oxidation of Primary Alcohols

2011-08-23

Jessica M. Hoover , Shannon S. Stahl

Aerobic oxidation reactions have been the focus of considerable attention, but their use in mainstream organic chemistry has been constrained by limitations in their synthetic scope and by practical factors, … Aerobic oxidation reactions have been the focus of considerable attention, but their use in mainstream organic chemistry has been constrained by limitations in their synthetic scope and by practical factors, such as the use of pure O2 as the oxidant or complex catalyst synthesis. Here, we report a new (bpy)CuI/TEMPO catalyst system that enables efficient and selective aerobic oxidation of a broad range of primary alcohols, including allylic, benzylic, and aliphatic derivatives, to the corresponding aldehydes using readily available reagents, at room temperature with ambient air as the oxidant. The catalyst system is compatible with a wide range of functional groups and the high selectivity for 1° alcohols enables selective oxidation of diols that lack protecting groups.

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Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride

1978-06-01

Anthony J. Mancuso , Shui‐Lung Huang , Daniel Swern

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chlorideAnthony J. Mancuso, Shui-Lung Huang, and Daniel SwernCite this: J. Org. Chem. 1978, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chlorideAnthony J. Mancuso, Shui-Lung Huang, and Daniel SwernCite this: J. Org. Chem. 1978, 43, 12, 2480–2482Publication Date (Print):June 1, 1978Publication History Published online1 May 2002Published inissue 1 June 1978https://pubs.acs.org/doi/10.1021/jo00406a041https://doi.org/10.1021/jo00406a041research-articleACS PublicationsRequest reuse permissionsArticle Views10170Altmetric-Citations1485LEARN 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

Hypervalent iodine reagents as a new entrance to organocatalysts

2009-01-01

Toshifumi Dohi , Yasuyuki Kita

The catalytic utilization of hypervalent iodine reagents, largely in consideration of economical and environmental viewpoints, is a most attractive strategy due to their unique features as extremely useful oxidants, with … The catalytic utilization of hypervalent iodine reagents, largely in consideration of economical and environmental viewpoints, is a most attractive strategy due to their unique features as extremely useful oxidants, with mild, safe, and environmentally friendly characteristics. In addition to a system based on electrochemical reoxidation conditions, new reliable catalytic methods have emerged in recent years that can broaden the scope of the catalytic concept. For these contributions, a catalytic strategy is now available for performing many representative types of oxidative bond-forming reactions and alcohol oxidations mediated by hypervalent iodines, some of which even include key transformations for natural product synthesis. A suitable choice of terminal oxidants, e.g., m-chloroperbenzoic acid (mCPBA) or Oxone®, for generation of active hypervalent iodine(III) or (V) species from iodoarenesin situ, has led to recent rapid expansion in this field. This feature article highlights the historical background and the efforts made to realize the catalytic utilization of these reagents, especially with focus on iodine(III).

Chemistry of Polyvalent Iodine

2008-11-06

Viktor V. Zhdankin , Peter J. Stang

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTChemistry of Polyvalent IodineViktor V. Zhdankin*† and Peter J. Stang‡View Author Information Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, and Department of … ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTChemistry of Polyvalent IodineViktor V. Zhdankin*† and Peter J. Stang‡View Author Information Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, and Department of Chemistry, 315 S 1400 E, Rm 2020, University of Utah, Salt Lake City, Utah 84112*Corresponding author (e-mail, [email protected]).†University of Minnesota Duluth.‡University of Utah.Cite this: Chem. Rev. 2008, 108, 12, 5299–5358Publication Date (Web):November 6, 2008Publication History Received5 May 2008Published online6 November 2008Published inissue 10 December 2008https://pubs.acs.org/doi/10.1021/cr800332chttps://doi.org/10.1021/cr800332creview-articleACS PublicationsCopyright © 2008 American Chemical SocietyRequest reuse permissionsArticle Views29668Altmetric-Citations1638LEARN 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:Alcohols,Iodine,Oxidation,Reagents,Salts Get e-Alerts

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Tetrapropylammonium Perruthenate, Pr4N+RuO4 -, TPAP: A Catalytic Oxidant for Organic Synthesis

1994-01-01

Steven V. Ley , Joanne Norman , William P. Griffith +1 more

This article reviews the oxidations of a wide range of molecules with tetrapropylammonium perruthenate including examples of both double oxidations and selective oxidations. Mechanistic studies are discussed and general experimental … This article reviews the oxidations of a wide range of molecules with tetrapropylammonium perruthenate including examples of both double oxidations and selective oxidations. Mechanistic studies are discussed and general experimental procedures are reported. In addition several interesting developments in the chemistry of this reagent are outlined, that is, heteroatom oxidation, cleavage reactions and also its use in sequential reaction processes. In order to present a complete picture examples of failed reactions have been included. 1. Introduction 1.1. Oxoruthenates 1.2. Mechanistic Studies on [RuO4]- as an Oxidant 1.3. Experimental Considerations 1.4. Functional Group Compatibility and Selectivity 2. Primary Hydroxyl Group Oxidation 3. Secondary Hydroxyl Group Oxidation 4. Allylic and Benzylic Hydroxyl Group Oxidation 5. Lactol Oxidation 6. Heteroatom Oxidation 7. Cleavage Reactions 8. Tandem or Sequential Reaction Processes 9. Failed Reactions 10. Conclusions

LXXIII.—Oxidation of tartaric acid in presence of iron

1894-01-01

H. J. H. Fenton

H. J. H. Fenton, J. Chem. Soc., Trans., 1894, 65, 899 DOI: 10.1039/CT8946500899 H. J. H. Fenton, J. Chem. Soc., Trans., 1894, 65, 899 DOI: 10.1039/CT8946500899

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Organic Polyvalent Iodine Compounds

1996-01-01

Peter J. Stang , Viktor V. Zhdankin

An improved catalytic OsO4 oxidation of olefins to -1,2-glycols using tertiary amine oxides as the oxidant

1976-06-01

V. VanRheenen , Robert C. Kelly , Dokun Cha

Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant

2012-01-01

Zhuangzhi Shi , Chun Zhang , Conghui Tang +1 more

For green and sustainable chemistry, molecular oxygen is considered as an ideal oxidant due to its natural, inexpensive, and environmentally friendly characteristics, and therefore offers attractive academic and industrial prospects. … For green and sustainable chemistry, molecular oxygen is considered as an ideal oxidant due to its natural, inexpensive, and environmentally friendly characteristics, and therefore offers attractive academic and industrial prospects. This critical review introduces the recent advances over the past 5 years in transition-metal catalyzed reactions using molecular oxygen as the oxidant. This review highlights the scope and limitations, as well as the mechanisms of these oxidation reactions (184 references).

Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation

2010-01-28

Mark S. Chen , M. Christina White

Methylene C-H bonds are among the most difficult chemical bonds to selectively functionalize because of their abundance in organic structures and inertness to most chemical reagents. Their selective oxidations in … Methylene C-H bonds are among the most difficult chemical bonds to selectively functionalize because of their abundance in organic structures and inertness to most chemical reagents. Their selective oxidations in biosynthetic pathways underscore the power of such reactions for streamlining the synthesis of molecules with complex oxygenation patterns. We report that an iron catalyst can achieve methylene C-H bond oxidations in diverse natural-product settings with predictable and high chemo-, site-, and even diastereoselectivities. Electronic, steric, and stereoelectronic factors, which individually promote selectivity with this catalyst, are demonstrated to be powerful control elements when operating in combination in complex molecules. This small-molecule catalyst displays site selectivities complementary to those attained through enzymatic catalysis.

Photochemical Reactions as Key Steps in Organic Synthesis

2008-02-27

Norbert Hoffmann

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhotochemical Reactions as Key Steps in Organic SynthesisNorbert HoffmannView Author Information Laboratoire des Réactions Sélectives et Applications, UMR 6519 CNRS et Université de Reims Champagne-Ardenne, UFR Sciences, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhotochemical Reactions as Key Steps in Organic SynthesisNorbert HoffmannView Author Information Laboratoire des Réactions Sélectives et Applications, UMR 6519 CNRS et Université de Reims Champagne-Ardenne, UFR Sciences, B.P. 1039, F-51687 Reims, Cedex 02, France Cite this: Chem. Rev. 2008, 108, 3, 1052–1103Publication Date (Web):February 27, 2008Publication History Received9 August 2006Published online27 February 2008Published inissue 1 March 2008https://pubs.acs.org/doi/10.1021/cr0680336https://doi.org/10.1021/cr0680336research-articleACS PublicationsCopyright © 2008 American Chemical SocietyRequest reuse permissionsArticle Views29807Altmetric-Citations1156LEARN 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:Chemical reactions,Cyclization,Hydrocarbons,Photochemical reactions,Reaction products Get e-Alerts

Large-Scale Oxidations in the Pharmaceutical Industry

2006-06-27

Stéphane Caron , Robert W. Dugger , Sally Gut Ruggeri +2 more

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTLarge-Scale Oxidations in the Pharmaceutical Industry†Stéphane Caron, Robert W. Dugger, Sally Gut Ruggeri, John A. Ragan, and David H. Brown RipinView Author Information Chemical Research and Development, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTLarge-Scale Oxidations in the Pharmaceutical Industry†Stéphane Caron, Robert W. Dugger, Sally Gut Ruggeri, John A. Ragan, and David H. Brown RipinView Author Information Chemical Research and Development, Pfizer Global Research Division, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340 Cite this: Chem. Rev. 2006, 106, 7, 2943–2989Publication Date (Web):June 27, 2006Publication History Received1 August 2005Published online27 June 2006Published inissue 1 July 2006https://pubs.acs.org/doi/10.1021/cr040679fhttps://doi.org/10.1021/cr040679fresearch-articleACS PublicationsCopyright © 2006 American Chemical SocietyRequest reuse permissionsArticle Views17142Altmetric-Citations684LEARN 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:Alcohols,Organic reactions,Oxidation,Oxides,Rearrangement Get e-Alerts

Solvent-Free Oxidation of Primary Alcohols to Aldehydes Using Au-Pd/TiO 2 Catalysts

2006-01-19

Dan I. Enache , Jennifer K. Edwards , Philip Landon +7 more

The oxidation of alcohols to aldehydes with O2 in place of stoichiometric oxygen donors is a crucial process for the synthesis of fine chemicals. However, the catalysts that have been … The oxidation of alcohols to aldehydes with O2 in place of stoichiometric oxygen donors is a crucial process for the synthesis of fine chemicals. However, the catalysts that have been identified so far are relatively inactive with primary alkyl alcohols. We showed that Au/Pd-TiO2 catalysts give very high turnover frequencies (up to 270,000 turnovers per hour) for the oxidation of alcohols, including primary alkyl alcohols. The addition of Au to Pd nanocrystals improved the overall selectivity and, using scanning transmission electron microscopy combined with x-ray photoelectron spectroscopy, we showed that the Au-Pd nanocrystals were made up of a Au-rich core with a Pd-rich shell, indicating that the Au electronically influences the catalytic properties of Pd.

Application of lanthanide reagents in organic synthesis

1992-01-01

Gary A. Molander

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTApplication of lanthanide reagents in organic synthesisGary A. MolanderCite this: Chem. Rev. 1992, 92, 1, 29–68Publication Date (Print):January 1, 1992Publication History Published online1 May 2002Published inissue 1 … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTApplication of lanthanide reagents in organic synthesisGary A. MolanderCite this: Chem. Rev. 1992, 92, 1, 29–68Publication Date (Print):January 1, 1992Publication History Published online1 May 2002Published inissue 1 January 1992https://pubs.acs.org/doi/10.1021/cr00009a002https://doi.org/10.1021/cr00009a002research-articleACS PublicationsRequest reuse permissionsArticle Views8477Altmetric-Citations1165LEARN 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

Green, Catalytic Oxidations of Alcohols

2002-06-20

Roger A. Sheldon , Isabel W. C. E. Arends , Gerd‐Jan ten Brink +1 more

Three methods are described, in the context of the guiding principles of green chemistry, for the catalytic oxidation of alcohols. The first employs a recyclable oligomeric TEMPO catalyst (PIPO) and … Three methods are described, in the context of the guiding principles of green chemistry, for the catalytic oxidation of alcohols. The first employs a recyclable oligomeric TEMPO catalyst (PIPO) and sodium hypochlorite as the oxidant in a bromide-free and chlorinated hydrocarbon solvent-free system. The second involves a ruthenium/TEMPO catalyst and oxygen as the oxidant. The third consists of a recyclable water-soluble palladium−diamine complex in conjunction with air as the oxidant in an aqueous biphasic system. The mechanisms of the ruthenium/TEMPO- and palladium-catalyzed oxidations are discussed, and the mechanism of the former is compared with that of the analogous copper/TEMPO catalyst.

Activation of C−H Bonds by Metal Complexes

1997-12-01

A. E. Shilov , Georgiy B. Shul’pin⊗

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTActivation of C−H Bonds by Metal ComplexesAlexander E. Shilov and Georgiy B. Shul'pinView Author Information N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 117977 … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTActivation of C−H Bonds by Metal ComplexesAlexander E. Shilov and Georgiy B. Shul'pinView Author Information N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 117977 Moscow, Russia Cite this: Chem. Rev. 1997, 97, 8, 2879–2932Publication Date (Web):December 18, 1997Publication History Received12 August 1996Revised8 July 1997Published online18 December 1997Published inissue 1 December 1997https://pubs.acs.org/doi/10.1021/cr9411886https://doi.org/10.1021/cr9411886research-articleACS PublicationsCopyright © 1997 American Chemical SocietyRequest reuse permissionsArticle Views65526Altmetric-Citations2615LEARN 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,Aromatic compounds,Hydrocarbons,Metals,Oxidation Get e-Alerts

Recent Advances in Transition Metal Catalyzed Oxidation of Organic Substrates with Molecular Oxygen

2005-05-06

Tharmalingam Punniyamurthy , Subbarayan Velusamy , Javed Iqbal

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRecent Advances in Transition Metal Catalyzed Oxidation of Organic Substrates with Molecular OxygenT. Punniyamurthy, Subbarayan Velusamy, and Javed IqbalView Author Information Department of Chemistry, Indian Institute of … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRecent Advances in Transition Metal Catalyzed Oxidation of Organic Substrates with Molecular OxygenT. Punniyamurthy, Subbarayan Velusamy, and Javed IqbalView Author Information Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India, and Dr. Reddy's Research Foundation, Miyapur, Hyderabad 500050, India Cite this: Chem. Rev. 2005, 105, 6, 2329–2364Publication Date (Web):May 6, 2005Publication History Received7 January 2005Published online6 May 2005Published inissue 1 June 2005https://pubs.acs.org/doi/10.1021/cr050523vhttps://doi.org/10.1021/cr050523vresearch-articleACS PublicationsCopyright © 2005 American Chemical SocietyRequest reuse permissionsArticle Views22251Altmetric-Citations1585LEARN 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:Catalysts,Hydrocarbons,Organic reactions,Oxidation,Oxygen Get e-Alerts

Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones

1983-11-01

D. B. DESS , J. C. Martin

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReadily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketonesD. B. Dess and J. C. MartinCite this: J. Org. Chem. 1983, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReadily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketonesD. B. Dess and J. C. MartinCite this: J. Org. Chem. 1983, 48, 22, 4155–4156Publication Date (Print):November 1, 1983Publication History Published online1 May 2002Published inissue 1 November 1983https://pubs.acs.org/doi/10.1021/jo00170a070https://doi.org/10.1021/jo00170a070research-articleACS PublicationsRequest reuse permissionsArticle Views26593Altmetric-Citations3081LEARN 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

Oxidation of alcohols by “activated” dimethyl sulfoxide. a preparative, steric and mechanistic study

1978-01-01

Kanji Omura , Daniel Swern

Indole synthesis: a review and proposed classification

2011-06-26

Douglass F. Taber , Pavan K. Tirunahari

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Thiyl Radicals in Organic Synthesis

2014-01-02

F. Dénès , Mark Pichowicz , Guillaume Povie +1 more

ADVERTISEMENT RETURN TO ISSUEReviewNEXTThiyl Radicals in Organic SynthesisFabrice Dénès*†, Mark Pichowicz‡, Guillaume Povie‡, and Philippe Renaud‡View Author Information† Laboratoire CEISAM UMR CNRS 6230 - UFR des Sciences et Techniques, Université … ADVERTISEMENT RETURN TO ISSUEReviewNEXTThiyl Radicals in Organic SynthesisFabrice Dénès*†, Mark Pichowicz‡, Guillaume Povie‡, and Philippe Renaud‡View Author Information† Laboratoire CEISAM UMR CNRS 6230 - UFR des Sciences et Techniques, Université de Nantes, 2 rue de la Houssinière, BP 92208 - 44322 Nantes Cedex 3, France‡ Department of Chemistry and Biochemistry, University of Berne, Freiestrasse 3, CH-3012 Bern, Switzerland*E-mail: [email protected]Cite this: Chem. Rev. 2014, 114, 5, 2587–2693Publication Date (Web):January 2, 2014Publication History Received13 August 2013Published online2 January 2014Published inissue 12 March 2014https://pubs.acs.org/doi/10.1021/cr400441mhttps://doi.org/10.1021/cr400441mreview-articleACS PublicationsCopyright © 2014 American Chemical SocietyRequest reuse permissionsArticle Views35344Altmetric-Citations758LEARN 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:Addition reactions,Cyclization,Hydrocarbons,Hydrogen abstraction,Thiols Get e-Alerts

Simple and selective method for aldehydes (RCHO) .fwdarw. (E)-haloalkenes (RCH:CHX) conversion by means of a haloform-chromous chloride system

1986-11-01

Kazuhiko Takai , Koji Nitta , K. UTIMOTO

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSimple and selective method for aldehydes (RCHO) .fwdarw. (E)-haloalkenes (RCH:CHX) conversion by means of a haloform-chromous chloride systemK. Takai, K. Nitta, and K. UtimotoCite this: J. Am. … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSimple and selective method for aldehydes (RCHO) .fwdarw. (E)-haloalkenes (RCH:CHX) conversion by means of a haloform-chromous chloride systemK. Takai, K. Nitta, and K. UtimotoCite this: J. Am. Chem. Soc. 1986, 108, 23, 7408–7410Publication Date (Print):November 1, 1986Publication History Published online1 May 2002Published inissue 1 November 1986https://pubs.acs.org/doi/10.1021/ja00283a046https://doi.org/10.1021/ja00283a046research-articleACS PublicationsRequest reuse permissionsArticle Views9474Altmetric-Citations689LEARN 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

Oxidative C−H Activation/C−C Bond Forming Reactions: Synthetic Scope and Mechanistic Insights

2005-05-03

Dipannita Kalyani , Nicholas R. Deprez , Lopa V. Desai +1 more

This paper describes a new palladium-catalyzed method for C−H activation/carbon−carbon bond formation with hypervalent iodine arylating agents. This transformation has been applied to a variety of arene and benzylic substrates … This paper describes a new palladium-catalyzed method for C−H activation/carbon−carbon bond formation with hypervalent iodine arylating agents. This transformation has been applied to a variety of arene and benzylic substrates containing different directing groups (pyridines, quinolines, oxazolidinones, and amides) and proceeds with high levels of regiocontrol. Mechanistic experiments provide preliminary evidence in support of an unusual mechanism for this transformation involving a Pd(II)/Pd(IV) catalytic cycle.

Fast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditions

1987-06-01

Pier Lucio Anelli , Carlo Biffi , Fernando Montanari +1 more

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTFast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditionsPier Lucio … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTFast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditionsPier Lucio Anelli, Carlo Biffi, Fernando Montanari, and Silvio QuiciCite this: J. Org. Chem. 1987, 52, 12, 2559–2562Publication Date (Print):June 1, 1987Publication History Published online1 May 2002Published inissue 1 June 1987https://pubs.acs.org/doi/10.1021/jo00388a038https://doi.org/10.1021/jo00388a038research-articleACS PublicationsRequest reuse permissionsArticle Views14918Altmetric-Citations691LEARN 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

Aerobic Copper-Catalyzed Organic Reactions

2013-06-20

Scott E. Allen , Ryan R. Walvoord , Rosaura Padilla‐Salinas +1 more

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTADDITION / CORRECTIONThis article has been corrected. View the notice.Aerobic Copper-Catalyzed Organic ReactionsScott E. Allen, Ryan R. Walvoord, Rosaura Padilla-Salinas, and Marisa C. Kozlowski*View Author Information Department … ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTADDITION / CORRECTIONThis article has been corrected. View the notice.Aerobic Copper-Catalyzed Organic ReactionsScott E. Allen, Ryan R. Walvoord, Rosaura Padilla-Salinas, and Marisa C. Kozlowski*View Author Information Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States*Tel: 215-898-3048. E-mail address: [email protected]Cite this: Chem. Rev. 2013, 113, 8, 6234–6458Publication Date (Web):June 20, 2013Publication History Received31 December 2012Published online20 June 2013Published inissue 14 August 2013https://pubs.acs.org/doi/10.1021/cr300527ghttps://doi.org/10.1021/cr300527greview-articleACS PublicationsCopyright © 2013 American Chemical SocietyRequest reuse permissionsArticle Views51660Altmetric-Citations1433LEARN 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:Catalysts,Copper,Hydrocarbons,Oxidation,Oxygen Get e-Alerts

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If CH Bonds Could Talk: Selective CH Bond Oxidation

2011-03-16

Timothy R. Newhouse , Phil S. Baran

Abstract CH oxidation has a long history and an ongoing presence in research at the forefront of chemistry and interrelated fields. As such, numerous highly useful articles and reviews have … Abstract CH oxidation has a long history and an ongoing presence in research at the forefront of chemistry and interrelated fields. As such, numerous highly useful articles and reviews have been written on this subject. Logically, these are generally written from the perspective of the scope and limitations of the reagents employed. This Minireview instead attempts to emphasize chemoselectivity imposed by the nature of the substrate. Consequently, many landmark discoveries in the field of CH oxidation are not discussed, but hopefully the perspective taken herein will allow CH oxidation reactions to be more readily incorporated into synthetic planning.

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Dearomatization Strategies in the Synthesis of Complex Natural Products

2011-04-19

Stéphane P. Roche , John A. Porco

Abstract Evolution in the field of the total synthesis of natural products has led to exciting developments over the last decade. Numerous chemoselective and enantioselective methodologies have emerged from total … Abstract Evolution in the field of the total synthesis of natural products has led to exciting developments over the last decade. Numerous chemoselective and enantioselective methodologies have emerged from total syntheses, resulting in efficient access to many important natural product targets. This Review highlights recent developments concerning dearomatization, a powerful strategy for the total synthesis of architecturally complex natural products wherein planar, aromatic scaffolds are converted to three‐dimensional molecular architectures.

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Recent Developments in the Chemistry of Polyvalent Iodine Compounds

2002-06-05

Viktor V. Zhdankin , Peter J. Stang

Reactivity of Dioxygen−Copper Systems

2004-01-13

Elizabeth A. Lewis , William B. Tolman

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReactivity of Dioxygen−Copper SystemsElizabeth A. Lewis and William B. TolmanView Author Information Department of Chemistry and Center for Metals in Biocatalysis, University of Minnesota, 207 Pleasant Street … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReactivity of Dioxygen−Copper SystemsElizabeth A. Lewis and William B. TolmanView Author Information Department of Chemistry and Center for Metals in Biocatalysis, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455 Cite this: Chem. Rev. 2004, 104, 2, 1047–1076Publication Date (Web):January 13, 2004Publication History Received9 July 2003Published online13 January 2004Published inissue 1 February 2004https://pubs.acs.org/doi/10.1021/cr020633rhttps://doi.org/10.1021/cr020633rresearch-articleACS PublicationsCopyright © 2004 American Chemical SocietyRequest reuse permissionsArticle Views11758Altmetric-Citations1195LEARN 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,Kinetics,Ligands,Organic reactions,Saturation Get e-Alerts

Green, Catalytic Oxidation of Alcohols in Water

2000-03-03

Gerd‐Jan ten Brink , Isabel W. C. E. Arends , Roger A. Sheldon

Alcohol oxidations are typically performed with stoichiometric reagents that generate heavy-metal waste and are usually run in chlorinated solvents. A water-soluble palladium(II) bathophenanthroline complex is a stable recyclable catalyst for … Alcohol oxidations are typically performed with stoichiometric reagents that generate heavy-metal waste and are usually run in chlorinated solvents. A water-soluble palladium(II) bathophenanthroline complex is a stable recyclable catalyst for the selective aerobic oxidation of a wide range of alcohols to aldehydes, ketones, and carboxylic acids in a biphasic water-alcohol system. The use of water as a solvent and air as the oxidant makes the reaction interesting from both an economic and environmental point of view.

Catalytic Oxidation of Organic Substrates by Molecular Oxygen and Hydrogen Peroxide by Multistep Electron Transfer—A Biomimetic Approach

2008-03-28

Julio Piera , Jan‐E. Bäckvall

Oxidation reactions are of fundamental importance in nature, and are key transformations in organic synthesis. The development of new processes that employ transition metals as substrate-selective catalysts and stoichiometric environmentally … Oxidation reactions are of fundamental importance in nature, and are key transformations in organic synthesis. The development of new processes that employ transition metals as substrate-selective catalysts and stoichiometric environmentally friendly oxidants, such as molecular oxygen or hydrogen peroxide, is one of the most important goals in oxidation chemistry. Direct oxidation of the catalyst by molecular oxygen or hydrogen peroxide is often kinetically unfavored. The use of coupled catalytic systems with electron-transfer mediators (ETMs) usually facilitates the procedures by transporting the electrons from the catalyst to the oxidant along a low-energy pathway, thereby increasing the efficiency of the oxidation and thus complementing the direct oxidation reactions. As a result of the similarities with biological systems, this can be dubbed a biomimetic approach.

Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen‐Coupled Turnover

2004-06-22

Shannon S. Stahl

Abstract Selective aerobic oxidation of organic molecules is a fundamental and practical challenge in modern chemistry. Effective solutions to this problem must overcome the intrinsic reactivity and selectivity challenges posed … Abstract Selective aerobic oxidation of organic molecules is a fundamental and practical challenge in modern chemistry. Effective solutions to this problem must overcome the intrinsic reactivity and selectivity challenges posed by the chemistry of molecular oxygen, and they must find application in diverse classes of oxidation reactions. Palladium oxidase catalysis combines the versatility of Pd II ‐mediated oxidation of organic substrates with dioxygen‐coupled oxidation of the reduced palladium catalyst to enable a broad range of selective aerobic oxidation reactions. Recent developments revealed that cocatalysts (e.g. Cu II , polyoxometalates, and benzoquinone) are not essential for efficient oxidation of Pd 0 by molecular oxygen. Oxidatively stable ligands play an important role in these reactions by minimizing catalyst decomposition, promoting the direct reaction between palladium and dioxygen, modulating organic substrate reactivity and permitting asymmetric catalysis.

Oxidation of Alcohols with Molecular Oxygen on Solid Catalysts

2004-04-01

Tamás Mallát , Alfons Baiker

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOxidation of Alcohols with Molecular Oxygen on Solid CatalystsTamas Mallat and Alfons BaikerView Author Information Institute for Chemical and Bioengineering, Swiss Federal Institute of Technology, ETH Hönggerberg, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOxidation of Alcohols with Molecular Oxygen on Solid CatalystsTamas Mallat and Alfons BaikerView Author Information Institute for Chemical and Bioengineering, Swiss Federal Institute of Technology, ETH Hönggerberg, HCI, CH-8093 Zurich, Switzerland Cite this: Chem. Rev. 2004, 104, 6, 3037–3058Publication Date (Web):April 1, 2004Publication History Received2 October 2003Published online1 April 2004Published inissue 1 June 2004https://pubs.acs.org/doi/10.1021/cr0200116https://doi.org/10.1021/cr0200116research-articleACS PublicationsCopyright © 2004 American Chemical SocietyRequest reuse permissionsArticle Views20705Altmetric-Citations1792LEARN 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:Alcohols,Catalysts,Metals,Oxidation,Oxygen Get e-Alerts

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016-02-10

Akira Yoshimura , Viktor V. Zhdankin

The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have … The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C-C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

Catalytic asymmetric dearomatization (CADA) reactions of phenol and aniline derivatives

2016-01-01

Wenting Wu , Liming Zhang , Shu‐Li You

Phenols are widely used as starting materials in both industrial and academic society. Dearomatization reactions of phenols provide an efficient way to construct highly functionalized cyclohexadienones. The main challenge to … Phenols are widely used as starting materials in both industrial and academic society. Dearomatization reactions of phenols provide an efficient way to construct highly functionalized cyclohexadienones. The main challenge to make them asymmetric by catalytic methods is to control the selectivity while overcoming the loss of aromaticity. In this tutorial review, an up to date summary of recent progress in CADA reactions of phenol and aniline derivatives is presented.

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Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide

1967-10-01

Jekishan R. Parikh , W. von E. Doering

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSulfur trioxide in the oxidation of alcohols by dimethyl sulfoxideJekishan R. Parikh and William v. E. DoeringCite this: J. Am. Chem. Soc. 1967, 89, 21, 5505–5507Publication Date … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSulfur trioxide in the oxidation of alcohols by dimethyl sulfoxideJekishan R. Parikh and William v. E. DoeringCite this: J. Am. Chem. Soc. 1967, 89, 21, 5505–5507Publication Date (Print):October 1, 1967Publication History Published online1 May 2002Published inissue 1 October 1967https://pubs.acs.org/doi/10.1021/ja00997a067https://doi.org/10.1021/ja00997a067research-articleACS PublicationsRequest reuse permissionsArticle Views14127Altmetric-Citations951LEARN 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

Scalable and sustainable electrochemical allylic C–H oxidation

2016-04-19

Evan J. Horn , Brandon R. Rosen , Yong Chen +4 more

Handbook of C–H Transformations

2005-08-24

Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions

2018-04-30

Jordan E. Nutting , Mohammad Rafiee , Shannon S. Stahl

N-Oxyl compounds represent a diverse group of reagents that find widespread use as catalysts for the selective oxidation of organic molecules in both laboratory and industrial applications. While turnover of … N-Oxyl compounds represent a diverse group of reagents that find widespread use as catalysts for the selective oxidation of organic molecules in both laboratory and industrial applications. While turnover of N-oxyl catalysts in oxidation reactions may be accomplished with a variety of stoichiometric oxidants, N-oxyl reagents have also been extensively used as catalysts under electrochemical conditions in the absence of chemical oxidants. Several classes of N-oxyl compounds undergo facile redox reactions at electrode surfaces, enabling them to mediate a wide range of electrosynthetic reactions. Electrochemical studies also provide insights into the structural properties and mechanisms of chemical and electrochemical catalysis by N-oxyl compounds. This review provides a comprehensive survey of the electrochemical properties and electrocatalytic applications of aminoxyls, imidoxyls, and related reagents, of which the two prototypical and widely used examples are 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and phthalimide N-oxyl (PINO).

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Catalytic Asymmetric Dihydroxylation

1994-12-01

Hartmuth C. Kolb , Michael S. VanNieuwenhze , K. Barry Sharpless

ADVERTISEMENT RETURN TO ISSUEPREVArticleCatalytic Asymmetric DihydroxylationHartmuth C. Kolb, Michael S. VanNieuwenhze, and K. Barry SharplessCite this: Chem. Rev. 1994, 94, 8, 2483–2547Publication Date (Print):December 1, 1994Publication History Published online1 May … ADVERTISEMENT RETURN TO ISSUEPREVArticleCatalytic Asymmetric DihydroxylationHartmuth C. Kolb, Michael S. VanNieuwenhze, and K. Barry SharplessCite this: Chem. Rev. 1994, 94, 8, 2483–2547Publication Date (Print):December 1, 1994Publication History Published online1 May 2002Published inissue 1 December 1994https://pubs.acs.org/doi/10.1021/cr00032a009https://doi.org/10.1021/cr00032a009research-articleACS PublicationsRequest reuse permissionsArticle Views36251Altmetric-Citations3457LEARN 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

Metal-catalyzed Oxidations of Organic Compounds

1981-01-01

Complete catalytic oxidation of volatile organics

1987-11-01

James J. Spivey

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTComplete catalytic oxidation of volatile organicsJames J. SpiveyCite this: Ind. Eng. Chem. Res. 1987, 26, 11, 2165–2180Publication Date (Print):November 1, 1987Publication History Published online1 May 2002Published inissue … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTComplete catalytic oxidation of volatile organicsJames J. SpiveyCite this: Ind. Eng. Chem. Res. 1987, 26, 11, 2165–2180Publication Date (Print):November 1, 1987Publication History Published online1 May 2002Published inissue 1 November 1987https://doi.org/10.1021/ie00071a001RIGHTS & PERMISSIONSArticle Views3903Altmetric-Citations741LEARN 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 PDF (3 MB) Get e-Alerts Get e-Alerts

The catalytic hydroamination of alkynes

2003-01-22

Frauke Pohlki , Sven Doye

The direct addition of ammonia or primary and secondary amines to non-activated alkenes and alkynes is potentially the most efficient approach towards the synthesis of higher substituted nitrogen-containing products. It … The direct addition of ammonia or primary and secondary amines to non-activated alkenes and alkynes is potentially the most efficient approach towards the synthesis of higher substituted nitrogen-containing products. It represents the most atom economic process for the formation of amines, enamines and imines, which are important bulk and fine chemicals or building blocks in organic synthesis. While the hydroamination of alkenes is still limited to more or less activated alkenes, great progress has been achieved in the case of alkynes over the last three years. To illustrate this progress, the review will mostly focus on recent developments in the field of intermolecular hydroamination of alkynes. However, if it is necessary for the discussion, older results and intramolecular reactions, which can be achieved more easily, will be mentioned as well.

In-Flow Oxidation of Primary Alcohols to Carboxylic Acids Using H2O2 and a Pt/SiO2 Catalyst

2025-06-23

| Synfacts

Unified Synthesis of Cycloheptatriene-Fused Heterobicyclo[3.1.1]heptanes by Lewis Acid-Catalyzed Higher-Order (8 + 3) Cycloaddition of Bicyclo[1.1.0]butanes with Troponoids

2025-06-23

Chao Peng , Youzhi Xu , Wenfeng Liu +5 more | Organic Letters

Herein, we developed a unified strategy to synthesize three libraries of medicinally attractive cycloheptatriene-fused heterobicyclo[3.1.1]heptanes (X-BCHeps, X = N, O, S) through a Lewis acid-catalyzed higher-order (8 + 3) cycloaddition … Herein, we developed a unified strategy to synthesize three libraries of medicinally attractive cycloheptatriene-fused heterobicyclo[3.1.1]heptanes (X-BCHeps, X = N, O, S) through a Lewis acid-catalyzed higher-order (8 + 3) cycloaddition of bicyclo[1.1.0]butanes (BCBs) with troponoids including azaheptafulvenes, tropones, and tropothiones. This method features excellent periselectivity, simple operation, mild conditions, and high efficiency. DFT calculations suggest that the cycloaddition proceeds via a concerted SN2 nucleophilic addition of troponoids to the Lewis acid-activated BCB species I. We anticipate that our findings will inspire the scientific community and motivate further exciting advances in BCB chemistry.

C(sp3)─S Bond Formation via the Synergy of Oxidative With Reductive Photocatalysts Through Photoredox and Dual Hydrogen Atom Transfer Processes

2025-06-23

Chao Zhou , Qiao Liang , X L Zhu +6 more | Advanced Science

A primary objective of organic synthesis is to establish a catalytic methodology that is mild, straightforward, and economically efficient. Thioesters are widely employed in the realms of physiology, pharmacology, and … A primary objective of organic synthesis is to establish a catalytic methodology that is mild, straightforward, and economically efficient. Thioesters are widely employed in the realms of physiology, pharmacology, and agriculture. It is imperative to continuously expand the range of sulfur-containing precursors to keep pace with the cutting-edge advancements in the field of organic sulfur chemistry. This research has uncovered that polysulfide anions (K2Sx), which serve as reducing catalysts, can also effectively act as sulfur reagents, providing the formation of C(sp3)-S bonds through a photoredox catalysis with an oxidative photocatalyst tetrabutylammonium decatungstate (TBADT) and dual hydrogen atom transfer (DHAT) process. In a pioneering study, a combinatorial strategy of an oxidative photocatalyst TBADT is presented with a reductive photocatalyst K2Sx, enabled a photo-induced three-component coupling reaction of simple aldehydes with alkanes containing C(sp3)─H and polysulfide anions. A numbers of thioester derivatives are successfully obtained in good yields, while a by-product H2S is captured and identified by gas chromatography analysis. Concurrently, density functional theory (DFT) calculations provided the theoretical support of the reaction mechanism.

A First Magnetic Bio-ionic Liquid for Catalytic Epoxidation of Alkenes

2025-06-23

Hakimeh Sharafinezhad , Reza Sandaroos , Saman Damavandi +1 more | Catalysis Letters

A Mn-salen Complex Supported on Carbon Nitride for Photoinduced Difunctionalization of Terminal Alkenes

2025-06-23

| Synfacts

Efficient Red Light‐Driven Singlet Oxygen Photocatalysis with an Osmium‐Based Coulombic Dyad

2025-06-23

Matthias Schmitz , Robert Naumann , Katja Heinze +1 more | Angewandte Chemie

Photoactive osmium complexes are widely used sensitizers for the generation of singlet oxygen, because they can be excited directly into their triplet states with low‐energy red light. However, their short‐lived … Photoactive osmium complexes are widely used sensitizers for the generation of singlet oxygen, because they can be excited directly into their triplet states with low‐energy red light. However, their short‐lived excited states reduce quenching efficiencies and reaction quantum yields significantly. To elongate the excited state lifetime, osmium complexes have been linked to organic chromophores to form molecular dyads. This approach, while effective, is time‐ and resource‐consuming, hampering larger‐scale applications. Here, we demonstrate a straightforward approach by directly mixing a readily available cationic osmium complex and an anionic perylene derivative in solution. Strong Coulombic interactions facilitate rapid energy transfer (~100 ps) from the excited osmium complex to the perylene derivative, mimicking a dyad‐like system. Detailed spectroscopic investigations revealed an increased singlet oxygen formation rate by over one order of magnitude at sub‐millimolar perylene concentrations, attributed to (i) the three orders of magnitude longer lifetime of the perylene triplet state produced via intra‐ion‐pair energy transfer and (ii) an inherently high singlet oxygen quantum yield of that key species. The novel catalyst system enables highly productive photooxygenations in water and in a MeOH/H2O 10/1 mixture, highlighting the broad applicability and versatility of the Coulombic dyad approach for photocatalytic synthesis and wastewater treatment.

Light Promoted Vinylogous Arbuzov Reaction with Electron Deficient Alkyl Halides

2025-06-22

Vladislav S. Kostromitin , Vyacheslav I. Supranovich , Alexander D. Dilman | Organic Letters

A vinylogous radical Arbuzov reaction involving the coupling of alkyl halides, terminal acetylenes, and triethyl phosphite furnishing vinyl phosphonates is described. Fluorinated iodides and α-bromoesters served as sources of radicals. … A vinylogous radical Arbuzov reaction involving the coupling of alkyl halides, terminal acetylenes, and triethyl phosphite furnishing vinyl phosphonates is described. Fluorinated iodides and α-bromoesters served as sources of radicals. The reaction is initiated by 400 nm light with or without photocatalyst, depending on the alkyl halide. The fluoroalkylation products could be further partially protodefluorinated using 1,3,5-trimethyltriazinane.

Copper-supported SBA-15 catalyst for the selective low-temperature gas phase aerobic oxidation of alcohols to aldehydes

2025-06-21

M. B. Patil , A.K. Mapari , Amit Deshmukh +1 more | Reaction Kinetics Mechanisms and Catalysis

Correction: Design and Catalytic Activity of a Cobalt(II) Acylpyrazolone Complex Anchored on MCM-48 for Selective Ethylbenzene Oxidation

2025-06-21

Grishma Vala , R.N. Jadeja , Aditya A. Puranik +1 more | Catalysis Letters

Selective photo-oxidation of lignin-based alcohols to aldehydes catalyzed by gold nanoparticles supported on titanate nanotubes and nanowires

2025-06-20

Henry Martínez Quiñónez , Álvaro A. Amaya , Fernando Martínez Ortega +2 more | Applied Catalysis A General

Noncovalent‐Interaction‐Dictated Product Selectivity in Intermolecular and Intramolecular Controllable Oxidation of Aromatic Amines Using 2,2′‐Diperoxyphenic Acid

2025-06-18

Li‐Ting Wang , Jingru Yin , Shaoyan Gan +3 more | Advanced Synthesis & Catalysis

Selective oxidation of aromatic amines is a valuable transformation in organic synthesis and medicinal chemistry as well as materials science. However, the efficient means to reach its full potential remain … Selective oxidation of aromatic amines is a valuable transformation in organic synthesis and medicinal chemistry as well as materials science. However, the efficient means to reach its full potential remain a formidable challenge because meticulous perturbations on the oxidation states can potentially lead to dramatically different product selectivity and efficacy profiles. Herein, by identifying bench‐stable and easily prepared 2,2′‐diperoxyphenic acid as oxidant and/or I 2 as additive, a general and divergent oxidation is developed to reliably form a wide assortment of nitrosobenzenes, nitrobenzenes, azobenzenes, and azoxybenzenes in an intermolecular and intramolecular controllable manner, avoiding the use of stoichiometric metal oxidants and transition metal‐based catalysts. Mechanistic studies reveal that the imposing of noncovalent interactions enables the achievement of reagent‐ and additive‐dependent reordering of NH bond reactivity and the rate of corresponding elementary steps.

Bhatt–Hauser Oxidation: A Site-Selective Late-Stage Benzylic C–H Oxidation

2025-06-18

Ketaki Ghosh , Dipakranjan Mal | Synlett

Abstract This account provides an overview of the copper-catalyzed, K2S2O8-mediated regioselective advanced-stage benzylic C–H oxidation, a process we have named as the Bhatt–Hauser oxidation. Its impact as a synthetic method, … Abstract This account provides an overview of the copper-catalyzed, K2S2O8-mediated regioselective advanced-stage benzylic C–H oxidation, a process we have named as the Bhatt–Hauser oxidation. Its impact as a synthetic method, especially in the context of the total synthesis of natural products, is presented. 1 Introduction 2 The Bhatt–Hauser Oxidation 3 Mechanism of the Bhatt–Hauser Oxidation 4 Modifications of the Bhatt–Hauser Oxidation 5 Synthesis of Formylanthraquinones and an Unprecedented Fragmentation 6 General Applications 7 Applications in the Total Synthesis of Natural Products: Advanced-Stage Oxidation 8 Conclusion

Electrochemical Chemo‐ and Regioselective Heterofunctionalization of Tropones via C(sp2)H Derivatization

2025-06-17

Mauro Garbini , Samuele Moncullo , Sofia Kiriakidi +6 more | Advanced Synthesis & Catalysis

A general electrochemical synthetic procedure for the site‐selective heterofunctionalization of activated tropones is documented. Detailed voltametric analysis and quantum chemistry calculations enabled the development of a predictive model for the … A general electrochemical synthetic procedure for the site‐selective heterofunctionalization of activated tropones is documented. Detailed voltametric analysis and quantum chemistry calculations enabled the development of a predictive model for the process efficiency, accounting for both reactivity and regioselectivity. Mono‐ and poly‐halogenation, nitration, sulfonation, and thiocyanation protocols are successfully executed starting from inexpensive sodium salts under oxidative electrolytic conditions (35 examples, isolated yields up to 95%, faradaic efficiencies up to 95%). The implementation of an iterative electrochemical/metal‐catalyzed cross‐coupling synthetic strategy, along with the adaptation of the protocol for the preparation of biologically relevant tropolone derivatives, underscores the generality and robustness of the methodology.

Photochemistry of Hypervalent Iodoazide Derivatives

2025-06-17

Nikita Gupta , Haoran Zhu , Joseph M. O’Shea +4 more | The Journal of Physical Chemistry A

The photochemical properties and reaction mechanisms of a series of hypervalent iodoazide compounds (R-IN3) were investigated, with substituents (-CH3, -H, -CF3) tuning the electronic density of the phenyl ring. With … The photochemical properties and reaction mechanisms of a series of hypervalent iodoazide compounds (R-IN3) were investigated, with substituents (-CH3, -H, -CF3) tuning the electronic density of the phenyl ring. With the help of UV irradiation, ultrafast time-resolved spectroscopy, and density functional theory (DFT) calculations, we elucidated the mechanisms of azide radical (N3•) release and its subsequent reactivity. UV-vis spectroscopy reveals that the photoconversion rates follow the trend CH3 > H > CF3, aligning with DFT-calculated ΔG values for ring-opening transitions. Homolytic cleavage of the I-N bond is identified as the dominant pathway for N3• generation upon UV irradiation, occurring within 400 fs. The released azide radicals react with the solvent molecules, while the iodo radical R-IC• fragments undergo a thermodynamically uphill lactone ring-opening (RO) reaction and subsequent hydrogen atom abstraction from the solvent to form carboxylic acids R-I-COOH, as validated by NMR and IR spectroscopy. The study also highlights the role of substituents in influencing reaction kinetics and intermediate stability, with electron-donating groups accelerating the release of the N3• species. This work bridges experimental observations with computational predictions, offering a foundation for future advancements in azide-based reactions and materials.

Tandem singlet oxygenation: Regioselective reaction of two <scp>1O2</scp> molecules by a nonconjugated diprenyl phenol

2025-06-16

Kamrun Nahar , Serah Essang , Lloyd Lapoot +1 more | Photochemistry and Photobiology

Tandem reactions of singlet oxygen (1O2) with nonconjugated natural products, such as plastoquinones, have attracted attention. However, mechanistic clarity is needed for the 1O2 uptake sequence and regioselectivity. Our strategy … Tandem reactions of singlet oxygen (1O2) with nonconjugated natural products, such as plastoquinones, have attracted attention. However, mechanistic clarity is needed for the 1O2 uptake sequence and regioselectivity. Our strategy was to study a tandem 1O2 reaction in a diprenylated phenol (geranyl phenol) bearing an inner and an outer prenyl group in the chain. Singlet oxygen first added to the inner prenyl group by H-bonding to the phenol OH, forming a gem-disubstituted and a tri-substituted dienyl dihydrobenzofuran. H2O2 was also released as a by-product. A second equivalent of 1O2 added by an "ene" reaction, but now to the outer rather than the inner site of the nonconjugated diene to reach four hydroperoxy-dihydrobenzofurans. There was no evidence for 1O2 "ene" reactions on the inner prenyl sites, but product decomposition included the formation of oxygen-centered radicals and even methane by a β-scission process. The results are an essential step in resolving mechanistic puzzles of reactive oxygen uptake in natural prenylated systems, which are important topics not only in physical-organic and synthetic chemistry but also in plant oxidation chemistry.

Unlocking Chromium Decarboxylative Ligand-to-Metal Charge Transfer: Efficient and Redox-Neutral Allylation of Aldehydes Using Carboxylic Acids

2025-06-16

Su‐Ying Wu , Ziqi Jiao , Alex T. Sung +3 more | Journal of the American Chemical Society

Here, we report the light-induced decarboxylative ligand-to-metal charge transfer (LMCT) of Cr(III) carboxylate complexes and demonstrate its applicability toward stereoselective Nozaki-Hiyama-Kishi (NHK) allylation reactions. The critical design element of our … Here, we report the light-induced decarboxylative ligand-to-metal charge transfer (LMCT) of Cr(III) carboxylate complexes and demonstrate its applicability toward stereoselective Nozaki-Hiyama-Kishi (NHK) allylation reactions. The critical design element of our reaction was identifying a bipyridyl ligand scaffold that enables a single Cr catalyst to facilitate both photolytic dissociation and aldehyde addition. This approach allows for the direct utilization of carboxylic acids and eliminates the need for external redox reagents. The broad utility of this protocol was demonstrated by the preparation of a variety of homoallylic alcohols in good yields and diastereoselectivities as well as the identification of advantageous retrosynthetic disconnections. Extensive studies supported the LMCT mechanism of this transformation, including the characterization of the catalytically active Cr-carboxylate species.

Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides

2025-06-13

A. Messina , F. Monticelli , Tiziano Miroglio +7 more | Molecules

Isocyanides insertions represent an important transformation in the palladium-catalyzed reactions landscape. However, one of their most significant limitations is in the use of inactivated alkyl electrophiles. Palladium photocatalysis has been … Isocyanides insertions represent an important transformation in the palladium-catalyzed reactions landscape. However, one of their most significant limitations is in the use of inactivated alkyl electrophiles. Palladium photocatalysis has been proven as a solid tool for the generation of alkyl radicals from alkyl halides, which may engage in subsequent transformations with a variety of reaction partners, closing the catalytic cycle. Herein, we report the mild three-component isocyanide insertions into inactivated alkyl iodides mediated by the catalytic activity of a photoexcited palladium complex. We investigated the scope of the reaction obtaining differently substituted secondary amides in good to high yields. We also investigated the mechanism, hypothesizing a key role of 4-(N,N-dimethylamino)pyridine in the outcome of the reaction.

Fine‐tuning the Photochemistry of Sulfur‐Based Linkages with Ruthenium(II) Polypyridyl Complexes for Optimal PACT Application

2025-06-12

Ramranjan Mishra , Pritha Chatterjee , Madhu Verma +2 more | Chemistry - A European Journal

The thioether‐based monodentate ligands are reported to be efficient photoreleased groups from Ru(II)‐photocages designed for photoactivated chemotherapy (PACT). However, the direct comparison and systematic studies of the photochemical behavior of … The thioether‐based monodentate ligands are reported to be efficient photoreleased groups from Ru(II)‐photocages designed for photoactivated chemotherapy (PACT). However, the direct comparison and systematic studies of the photochemical behavior of sulfur linkages of varied electronic/oxidation states, i.e., sulfoxides, thioethers, or thiols coordinated with Ru(II)‐polypyridyls, remain unexplored. To delve into the intricate photophysics and photochemistry of Ru(II)‐S linkages, two Ru(II)‐polypyridyls: [Ru(ttpy)(phen)(DMSO)](PF6)2 [1](PF6)2, [Ru(ttpy)(phen)(DAS)](PF6)2 [2](PF6)2, [ttpy = 4′‐tolyl‐2,2′:6′,2″‐terpyridine, phen = 1,10‐phenanthroline, DAS = diallyl sulfide, DMSO = dimethyl sulfoxide] were synthesized. Here, we used DMSO for the typical sulfoxide linkage, while DAS a biologically potent phytochemical, probed as a thioether linkage with Ru(II). The photosolvolysis monitored by UV−vis and 1H NMR studies with white LED in MeCN indicated slower substitution of DMSO than DAS. The water‐soluble [1](NO3)2 and [2](NO3)2 exhibit facile photorelease of DAS than DMSO from {Ru(ttpy)(phen)}2+‐photocages in water. The cytotoxicity and photocytotoxicity studies with HeLa and Caco2 cells show that [2](PF6)2 and [2](NO3)2 were more photocytotoxic with higher photoindices compared to [1](PF6)2 and [1](NO3)2. This apparently led to the conclusion that markedly facile photorelease of DAS resulted in higher photocytotoxicity of the DAS‐based complexes. Therefore, thioether‐based Ru(II)‐polypyridyls portray better options for photocaging of prodrugs and PACT applications.

Synthesis of Isoquinoline N-Oxides via Hypervalent Iodine-Mediated Oxidative Cyclization of Ketoximes with Alkenes

2025-06-05

Aurapat Ngamnithiporn , Padon Chuentragool , Supakarn Punnita +6 more | The Journal of Organic Chemistry

Reported herein is the development of an intramolecular oxidative cyclization of ketoximes with alkenes for the preparation of isoquinoline N-oxides. The reaction, which utilizes phenyliodine bis(trifluoroacetate) (PIFA) as an oxidant … Reported herein is the development of an intramolecular oxidative cyclization of ketoximes with alkenes for the preparation of isoquinoline N-oxides. The reaction, which utilizes phenyliodine bis(trifluoroacetate) (PIFA) as an oxidant and 2,2,2-trifluoroethanol (TFE) as a solvent, proceeds to afford various N-heterocyclic products, including aryl/heteroaryl-fused pyridine N-oxides, isoindole N-oxides, and 2-benzazepine derivatives. Preliminary experimental and computational mechanistic studies suggest that the ionic pathway is the primary mechanism. The synthetic utility of the developed method was highlighted via several product transformations.

The crystal structure of 2-benzoyl-3′,4′,5′,6′-tetrahydrospiro[isoindoline-1,2′-pyran]-3-one, C19H17NO3

2025-06-05

Tao-Tao Zhao , Jia‐Qiang Wu , Haiping Wang | Zeitschrift für Kristallographie - New Crystal Structures

Abstract C 19 H 17 NO 3 , monoclinic, P 2 1 / c (no. 14), a = 9.0838(4) Å, b = 9.9597(4) Å, c = 16.9190(7) Å, β = … Abstract C 19 H 17 NO 3 , monoclinic, P 2 1 / c (no. 14), a = 9.0838(4) Å, b = 9.9597(4) Å, c = 16.9190(7) Å, β = 91.0780°, V = 1530.42(11) Å 3 , Z = 4, R gt ( F ) = 0.0465, wR ref ( F 2 ) = 0.1208, T = 170 K.

Synthesis, Structure, and Magnetic Properties of a Copper(II)‐Nitroxide Chain and Its Catalytic Activity Toward Congo Red Decolorization

2025-06-03

Thomaz de A. Costa , Júlio César Rocha , Victor M. S. Veiga +6 more | Applied Organometallic Chemistry

ABSTRACT A new compound [Cu(hfac) 2 (msTEMPO)] n , where hfac − is hexafluoroacetylacetonate and msTEMPO is the TEMPO derivative radical 4‐methanesulfonyl‐oxy‐2,2,6,6‐tetramethylpiperidine‐1‐oxyl , was synthesized, and its magnetic behavior and … ABSTRACT A new compound [Cu(hfac) 2 (msTEMPO)] n , where hfac − is hexafluoroacetylacetonate and msTEMPO is the TEMPO derivative radical 4‐methanesulfonyl‐oxy‐2,2,6,6‐tetramethylpiperidine‐1‐oxyl , was synthesized, and its magnetic behavior and catalytic activity toward the decolorization of Congo red (CR) were investigated. The crystal structure was determined by single crystal X‐ray diffraction technique, and it is described as a one‐dimensional compound with the nitroxide radical bridge‐coordinated in head‐to‐head mode to copper(II) ions. The magnetic investigation performed by magnetometry and EPR techniques revealed a TEMPO‐copper(II)‐TEMPO ferromagnetic interaction with J = +18 cm −1 . The catalytic activity was evaluated through Congo red oxidation under controlled conditions (phosphate buffer, pH = 8.5) in H 2 O 2 with the molar ratio of [Cu(hfac) 2 (msTEMPO)] n : CR: H 2 O 2 of 1: 30: X, where X = 80, 140, 200, 400, 1000, and 2000. The kinetics and rate of decolorization were obtained for all conditions where the best result for the decolorization rate was observed for the condition of 1:30:200 with 55% of decolorization ratio in 1 h against 0.5% of the uncatalyzed reaction.

Engineering immobilized 2,2,6,6-tetramethylpiperidine-1-oxyl catalysts via covalent anchoring for selective aerobic oxidation of benzyl alcohol to benzaldehyde

2025-06-01

Guojun Shi , Fan Xu , Wenjie Yang +1 more | Colloids and Surfaces A Physicochemical and Engineering Aspects

Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[d]pyrimidin]-4-one core

2025-06-01

Nikolai A. Arutiunov , С. В. Щербаков , Daria A. Shtal +5 more | Tetrahedron