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A Mechanistic Dichotomy Leading to a Ruthenium‐Catalyzed cis ‐Addition for Stereoselective Formation of ( Z )‐Vinyl Bromides
Author(s) -
Trost Barry M.,
Pinkerton Anthony B.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000117)39:2<360::aid-anie360>3.0.co;2-9
Subject(s) - chemoselectivity , alkyne , stereoselectivity , ruthenium , chemistry , lithium (medication) , bromide , vinyl bromide , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry , medicine , endocrinology
Either trans‐ or cis ‐haloalkylation is possible through a three‐component coupling [Eq. (1)]. The cis ‐bromoruthenation of an alkyne by lithium bromide and [CpRu(CH 3 CN) 3 ]PF 6 , catalyzed by SnBr 4 , gives ( Z )‐vinyl bromides with high chemoselectivity. The degree of control over the sterochemistry raises intriguing mechanistic questions as well as offering practical synthetic utility.