4.8 Article

Silver-Catalyzed Arylation of (Hetero)arenes by Oxidative Decarboxylation of Aromatic Carboxylic Acids

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 7, Pages 2199-2203

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408630

Keywords

C-H activation; heterocycles; oxidation; radicals; silver

Funding

  1. 973 Program [2011CB932404, 2011CBA00501]
  2. NSFC [21332001, 21431008, 21301173]
  3. CAS/SAFEA International Partnership Program for Creative Research Teams

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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.

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