Organic Chemistry Portal



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:

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

DOI: 10.1021/acs.orglett.1c00820

see article for more reactions


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.

see article for more examples

proposed mechanism

Key Words

thiocyanates, vinyl sulfones, multicomponent reactions, potassium peroxydisulfate

ID: J54-Y2021