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Metal-Free Radical Thiocyanatosulfonation of Terminal Alkynes in Aqueous Medium

Mingmei Zhang and Xianghua Zeng*

*College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, P. R. China, Email: xianghuazengzjxu.edu.cn

M. Zhang, X. Zeng, Org. Lett., 2021, 23, 3326-3330.

DOI: 10.1021/acs.orglett.1c00820 (free Supporting Information)


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Abstract

A 1,2-thiocyanatosulfonation of terminal alkynes with NH4SCN and sulfonyl hydrazides provides (E)-β-(thiocyanato)vinyl sulfones via a radical pathway. This metal-free reaction offers mild conditions, readily available reagents, a broad substrate scope, good functional group compatibility, and excellent stereoselectivity.

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proposed mechanism



Key Words

thiocyanates, vinyl sulfones, multicomponent reactions, potassium peroxydisulfate


ID: J54-Y2021