The Green ChemisTREE: 20 years after taking root with the 12 principles

Green Chemistry, Journal Year: 2018, Volume and Issue: 20(9), P. 1929 - 1961

Published: Jan. 1, 2018

A broad overview of the achievements and emerging areas in field Green Chemistry.

Language: Английский

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The electron is a catalyst

Nature Chemistry, Journal Year: 2014, Volume and Issue: 6(9), P. 765 - 773

Published: Aug. 21, 2014

Language: Английский

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Electrochemical Oxidative Cross-Coupling with Hydrogen Evolution Reactions

Accounts of Chemical Research, Journal Year: 2019, Volume and Issue: 52(12), P. 3309 - 3324

Published: Nov. 27, 2019

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

Language: Английский

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Recent Advances in C–H Functionalization

The Journal of Organic Chemistry, Journal Year: 2016, Volume and Issue: 81(2), P. 343 - 350

Published: Jan. 15, 2016

ADVERTISEMENT RETURN TO ISSUEEditorialNEXTRecent Advances in C–H FunctionalizationHuw M. L. Davies and Daniel MortonView Author Information Department of Chemistry, Emory UniversityCite this: J. Org. Chem. 2016, 81, 2, 343–350Publication Date (Web):January 15, 2016Publication History Published online15 January 2016Published inissue 15 2016https://pubs.acs.org/doi/10.1021/acs.joc.5b02818https://doi.org/10.1021/acs.joc.5b02818editorialACS PublicationsCopyright © 2016 American Chemical Society. This publication is available under these Terms Use. Request reuse permissions free to access through this site. Learn MoreArticle Views42947Altmetric-Citations516LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated reflect usage leading up last few days.Citations number other articles citing article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence for given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail (2 MB) Get e-AlertscloseSUBJECTS:Aromatic compounds,Catalysts,Chemical reactions,Functionalization,Selectivity e-Alerts

Language: Английский

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Manganese-Catalyzed C–H Activation

ACS Catalysis, Journal Year: 2016, Volume and Issue: 6(6), P. 3743 - 3752

Published: April 27, 2016

Manganese is found in the active center of numerous enzymes that operate by an outer-sphere homolytic C–H cleavage. Thus, a plethora bioinspired radical-based functionalizations manganese catalysis have been devised during past decades. In contrast, organometallic activation means has emerged only recently as increasingly viable tool organic synthesis. These manganese(I)-catalyzed processes enabled variety with ample scope, which very set stage for substitutive functionalizations. The versatile largely operates isohypsic, thus redox-neutral, mode action through chelation assistance, and provided step-economical access to structurally divers compounds relevance inter alia bioorganic, agrochemical, medicinal chemistry well material sciences.

Language: Английский

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C–H Functionalization in the Synthesis of Amino Acids and Peptides

Chemical Reviews, Journal Year: 2014, Volume and Issue: 114(18), P. 8775 - 8806

Published: Aug. 21, 2014

ADVERTISEMENT RETURN TO ISSUEReviewNEXTC–H Functionalization in the Synthesis of Amino Acids and PeptidesAnaïs F. M. Noisier Margaret A. Brimble*View Author Information School Chemical Sciences Maurice Wilkins Centre for Molecular Biodiscovery, The University Auckland, 23 Symonds Street, Auckland Central 1010, New Zealand*E-mail: [email protected]Cite this: Chem. Rev. 2014, 114, 18, 8775–8806Publication Date (Web):August 21, 2014Publication History Received9 April 2014Published online21 August inissue 24 September 2014https://doi.org/10.1021/cr500200xCopyright © 2014 American SocietyRIGHTS & PERMISSIONSACS AuthorChoiceArticle Views18448Altmetric-Citations444LEARN ABOUT THESE METRICSArticle Views are COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InReddit (8 MB) Get e-AlertsSUBJECTS:Anions,Arylation,Functionalization,Monomers,Peptides proteins e-Alerts

Language: Английский

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Copper-Catalyzed Aerobic Oxidations of Organic Molecules: Pathways for Two-Electron Oxidation with a Four-Electron Oxidant and a One-Electron Redox-Active Catalyst

Accounts of Chemical Research, Journal Year: 2015, Volume and Issue: 48(6), P. 1756 - 1766

Published: May 28, 2015

Selective oxidation reactions have extraordinary value in organic chemistry, ranging from the conversion of petrochemical feedstocks into industrial chemicals and polymer precursors to introduction heteroatom functional groups pharmaceutical agrochemical intermediates. Molecular oxygen (O2) would be ideal oxidant for these transformations. Whereas many commodity-scale oxidations simple hydrocarbon employ O2 as an oxidant, methods selective more complex molecules bearing diverse are often incompatible with existing aerobic methods. The latter limitation provides basis our interest development new catalytic transformations elucidation mechanistic principles that underlie reactions. One challenge inherent such is incommensurate redox stoichiometry associated use O2, a four-electron achieve two-electron molecules. This issue further complicated by first-row transition-metal catalysts, which tend undergo facile one-electron steps. In recent years, we been investigating Cu-catalyzed wherein complexities just noted clearly evident. Account surveys work this area, has emphasized three general classes reactions: (1) single-electron-transfer oxidative functionalization electron-rich substrates, arenes heterocycles; (2) carbon-heteroatom bond-forming reactions, including C-H oxidations, proceed via organocopper(III) intermediates; (3) alcohols amines Cu(II) combination redox-active cocatalyst dehydrogenate bond. These reaction demonstrate different pathways cooperative involvement two oxidants, either species or nitroxyl cocatalyst. They show ability Cu participate traditional organometallic steps commonly precious-metal activation reductive elimination, but also accessibility not typically single-electron transfer. Many offer advantages over analogous mediated palladium other noble metals. For example, coupling first above capable using terminal while Pd require less desirable hypervalent iodine electrophilic halogen sources. addition, alcohol amine third class significantly efficient much broader scope group tolerance than related Pd-catalyzed differences described herein.

Language: Английский

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C−H Functionalisation for Hydrogen Isotope Exchange

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 57(12), P. 3022 - 3047

Published: Oct. 12, 2017

The various applications of hydrogen isotopes (deuterium, D, and tritium, T) in the physical life sciences demand a range methods for their installation an array molecular architectures. In this Review, we describe recent advances synthetic C-H functionalisation isotope exchange.

Language: Английский

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Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C–H Activation Reactions

Chemistry Letters, Journal Year: 2015, Volume and Issue: 44(4), P. 410 - 421

Published: Jan. 26, 2015

Abstract This review focuses on chelation-assisted regioselective C–H activation with C–C or/and C–N bond formation using nickel(0) or -(II) as the catalysts, where bidentate directing groups play a key role in successful transformation. A 2-pyridinylmethylamine an 8-aminoquinoline moiety are more powerful auxiliaries among examined.

Language: Английский

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External Oxidant-Free Oxidative Cross-Coupling: A Photoredox Cobalt-Catalyzed Aromatic C–H Thiolation for Constructing C–S Bonds

Journal of the American Chemical Society, Journal Year: 2015, Volume and Issue: 137(29), P. 9273 - 9280

Published: July 9, 2015

An external oxidant-free oxidative coupling for aromatic C-H thiolation by visible-light photoredox cobalt-catalysis has been developed. Various substrates could afford benzothiazoles in good to excellent yields, and only H2 is generated as a side product. When catalytic TBAOH was used the base, not 2-aryl but also 2-alkylbenzothiazoles be obtained through this novel dehydrogenative reaction. This method scaled up applied synthesis of biologically active molecules bearing benzothiazole structural scaffolds (potent antitumor agents). Furthermore, unexpected oxidation byproduct amides, which are often cyclization thiobenzanilides, can completely avoided. Mechanistic studies showed that originates from substrates. The kinetic indicate interaction between cobalt catalyst proton might involved rate-limiting process.

Language: Английский

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