Literature DB >> 25537369

Silver-catalyzed arylation of (hetero)arenes by oxidative decarboxylation of aromatic carboxylic acids.

Jian Kan1, Shijun Huang, Jin Lin, Min Zhang, Weiping Su.   

Abstract

A long-standing challenge in Minisci reactions is achieving the arylation of heteroarenes by oxidative decarboxylation of aromatic carboxylic acids. To address this challenge, the silver-catalyzed intermolecular Minisci reaction of aromatic carboxylic acids was developed. With an inexpensive silver salt as a catalyst, this new reaction enables a variety of aromatic carboxylic acids to undergo decarboxylative coupling with electron-deficient arenes or heteroarenes regardless of the position of the substituents on the aromatic carboxylic acid, thus eliminating the need for ortho-substituted aromatic carboxylic acids, which were a limitation of previously reported methods.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; heterocycles; oxidation; radicals; silver

Mesh:

Substances:

Year:  2014        PMID: 25537369     DOI: 10.1002/anie.201408630

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  15 in total

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2.  Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling.

Authors:  Chengwei Liu; Chong-Lei Ji; Tongliang Zhou; Xin Hong; Michal Szostak
Journal:  Angew Chem Int Ed Engl       Date:  2021-04-06       Impact factor: 15.336

Review 3.  Radicals: Reactive Intermediates with Translational Potential.

Authors:  Ming Yan; Julian C Lo; Jacob T Edwards; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

4.  Simple, Efficient and Controllable Synthesis of Iodo/Di-iodoarenes via Ipsoiododecarboxylation/Consecutive Iodination Strategy.

Authors:  Yun Yang; Lijuan Zhang; Guo-Jun Deng; Hang Gong
Journal:  Sci Rep       Date:  2017-01-16       Impact factor: 4.379

Review 5.  Recent Progress in Decarboxylative Oxidative Cross-Coupling for Biaryl Synthesis.

Authors:  Gregory J P Perry; Igor Larrosa
Journal:  European J Org Chem       Date:  2017-04-26

6.  Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals.

Authors:  L Candish; M Freitag; T Gensch; F Glorius
Journal:  Chem Sci       Date:  2017-02-27       Impact factor: 9.825

7.  Photo-driven redox-neutral decarboxylative carbon-hydrogen trifluoromethylation of (hetero)arenes with trifluoroacetic acid.

Authors:  Jin Lin; Zhi Li; Jian Kan; Shijun Huang; Weiping Su; Yadong Li
Journal:  Nat Commun       Date:  2017-02-06       Impact factor: 14.919

8.  Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

Authors:  Yuhei Katsuma; Hiroki Asakawa; Makoto Yamashita
Journal:  Chem Sci       Date:  2017-12-11       Impact factor: 9.825

9.  The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions towards Phenanthrene Derivatives.

Authors:  Xuchen Zhao; Jon D Rainier
Journal:  Synthesis (Stuttg)       Date:  2021-01-11       Impact factor: 3.157

10.  Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3 coupling of carboxylic acids and π-electrophiles.

Authors:  Kaitie C Cartwright; Jon A Tunge
Journal:  Chem Sci       Date:  2020-07-16       Impact factor: 9.825

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