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Regio‐ and Stereoselective Synthesis of Vicinal ( Z )‐Dihaloalkenylsilanes from Silyl Ethynylarenes
Author(s) -
Yauchi Yuta,
Ide Masataka,
Shiogai Ryo,
Chikugo Takuya,
Iwasawa Tetsuo
Publication year - 2015
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.201403450
Subject(s) - chemistry , stereoselectivity , vicinal , halogenation , silylation , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The direct access to ( Z )‐(1‐bromo‐2‐chloro‐2‐arylvinyl)triisopropylsilane through formal addition of BrCl to triisopropylsilyl ethynylarene was explored. BrCl was generated in situ from commercially available TMSCl and N ‐bromosuccinimide. This simple protocol enabled highly efficient regio‐ and stereoselective bromochlorination, bis‐bromination, and bis‐chlorination of the triple bond on a gram scale in the syn mode. It thus provided a potentially diverse scaffold for adaptable preparation of differently all‐carbon tetrasubstituted olefins.