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General Approach to Amides through Decarboxylative Radical Cross-Coupling of Carboxylic Acids and Isocyanides.
Yan, Qing; Yuan, Qing-Jia; Shatskiy, Andrey; Alvey, Gregory R; Stepanova, Elena V; Liu, Jian-Quan; Kärkäs, Markus D; Wang, Xiang-Shan.
  • Yan Q; School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.
  • Yuan QJ; School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.
  • Shatskiy A; Department of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden.
  • Alvey GR; Department of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden.
  • Stepanova EV; Department of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden.
  • Liu JQ; Research School of Chemistry & Applied Biomedical Sciences, Tomsk Polytechnic University, Lenin Avenue 30, 634050 Tomsk, Russia.
  • Kärkäs MD; School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.
  • Wang XS; Department of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden.
Org Lett ; 26(16): 3380-3385, 2024 Apr 26.
Article en En | MEDLINE | ID: mdl-38607963
ABSTRACT
Herein, we report a silver-catalyzed protocol for decarboxylative cross-coupling between carboxylic acids and isocyanides, leading to linear amide products through a free-radical mechanism. The disclosed approach provides a general entry to a variety of decorated amides, accommodating a diverse array of radical precursors, including aryl, heteroaryl, alkynyl, alkenyl, and alkyl carboxylic acids. Notably, the protocol proved to be efficient for decarboxylative late-stage functionalization of several elaborate pharmaceuticals, demonstrating its potential applications.