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通过羧酸与异腈的脱羧自由基交叉偶联制备酰胺的通用方法。

General Approach to Amides through Decarboxylative Radical Cross-Coupling of Carboxylic Acids and Isocyanides.

作者信息

Yan Qing, Yuan Qing-Jia, Shatskiy Andrey, Alvey Gregory R, Stepanova Elena V, Liu Jian-Quan, Kärkäs Markus D, Wang Xiang-Shan

机构信息

School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.

Department of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden.

出版信息

Org Lett. 2024 Apr 26;26(16):3380-3385. doi: 10.1021/acs.orglett.4c00872. Epub 2024 Apr 12.

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.

摘要

在此,我们报道了一种银催化的羧酸与异腈之间的脱羧交叉偶联反应方法,该反应通过自由基机理生成直链酰胺产物。所公开的方法为各种修饰酰胺提供了一种通用的合成途径,可容纳多种自由基前体,包括芳基、杂芳基、炔基、烯基和烷基羧酸。值得注意的是,该方法被证明对于几种复杂药物的脱羧后期官能团化是有效的,展示了其潜在的应用价值。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d532/11059110/b9235b5921c7/ol4c00872_0001.jpg

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