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A Transition-Metal-Free Synthesis of Arylcarboxyamides from Aryl Diazonium Salts and Isocyanides

Zhonghua Xia and Qiang Zhu*

*Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, China, Email: zhu_qianggibh.ac.cn

Z. Xia, Q. Zhu, Org. Lett., 2013, 15, 4110-4113.

DOI: 10.1021/ol4017244 (free Supporting Information)


Abstract

A transition-metal-free carboxyamidation process, using aryl diazonium tetrafluoroborates and isocyanides under mild conditions, is initiated by a base and solvent induced aryl radical, followed by radical addition to isocyanide and single electron transfer (SET) oxidation. The reaction affords the corresponding arylcarboxyamide upon hydration of the nitrilium intermediate.

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Key Words

arylcarboxyamides


ID: J54-Y2013