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Silver‐Catalyzed Regio‐ and Stereoselective Thiocyanation of Haloalkynes: Access to ( Z )‐Vinyl Thiocyanates
Author(s) -
Jiang Guangbin,
Zhu Chuanle,
Li Jianxiao,
Wu Wanqing,
Jiang Huanfeng
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601142
Subject(s) - chemistry , stereoselectivity , catalysis , substrate (aquarium) , halogen , ligand (biochemistry) , amine gas treating , combinatorial chemistry , thiocyanate , organic chemistry , biochemistry , oceanography , alkyl , receptor , geology
A regio‐ and stereoselective method for the preparation of ( Z )‐vinyl thiocyanate derivatives by silver‐catalyzed thiocyanation of haloalkynes is reported. This method features practical, free of ligand, broad substrate scope, excellent stereoselectivity and gram‐scale synthesis. Significantly, the halogen atom of haloalkynes is retained, which allows the synthesis of 2,5‐diphenylthiophene, thiazol‐2‐amine and trifluoromethyl sulfides derivatives via simple transformation.