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Au‐Catalyzed Addition of Nucleophiles to Chloroalkynes: A Regio‐ and Stereoselective Synthesis of ( Z )‐Alkenyl Chlorides
Author(s) -
Liu Congrong,
Xue Yunbo,
Ding Lianghui,
Zhang Haiyun,
Yang Fulai
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801222
Subject(s) - stereoselectivity , chemistry , nucleophile , catalysis , regioselectivity , nucleophilic addition , organic chemistry , medicinal chemistry , stereochemistry
An unprecedented protocol has been developed for the regio‐ and stereoselective synthesis of ( Z )‐alkenyl chlorides via the gold‐catalyzed addition of nucleophiles to chloroalkynes. In the presence of 1 mol‐% BrettPhosAuCl, a broad range of nucleophiles smoothly react with aromatic, vinylic, or aliphatic chloroalkynes to afford various functionalized ( Z )‐alkenyl chlorides with high to excellent yields and extremely high stereoselectivity.