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- Title
Regio- and Stereoselective Synthesis of Vicinal ( Z)-Dihaloalkenylsilanes from Silyl Ethynylarenes.
- Authors
Yauchi, Yuta; Ide, Masataka; Shiogai, Ryo; Chikugo, Takuya; Iwasawa, Tetsuo
- Abstract
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.
- Subjects
STEREOSELECTIVE reactions; VINYL halides; SILYL ethers; BROMOCHLOROMETHANE; SILANE compounds; CHEMICAL synthesis; HYDROCARBONS spectra; ALKENES; BROMINATION
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 5, p938
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403450