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Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides

Pei Yu, Yuwei Wang, Zhigang Zeng* and Yunfeng Chen*

*Hubei University of Science and Technology, Xianning 437100; Wuhan Institute of Technology, Wuhan 430073, China, Email:,

P. Yu, Y. Wang, Z. Zeng, Y. Chen, J. Org. Chem., 2019, 84, 14883-14891.

DOI: 10.1021/acs.joc.9b02211


A metal-free oxidative-amidation strategy enables the synthesis of α-ketothioamides and amides from α-azido ketones. The C-H bond thionation of α-azido ketones with elemental sulfur could form α-ketothioacyl azide, which was then nucleophilically attacked by amines, while amides could be formed with the release of nitrogen gas and cyano anion in the presence of PhI(OAc)2.

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Key Words

thioamides (thionation, amination), multicomponent reactions, oxidative amidation, PIDA

ID: J42-Y2019