A Mechanistic Dichotomy Leading to a Ruthenium-Catalyzedcis-Addition for Stereoselective Formation of (Z)-Vinyl Bromides

作者：Barry M. Trost, Anthony B. Pinkerton · 发表于：Angewandte Chemie International Edition · 年份：2000 · DOI：10.1002/(sici)1521-3773(20000117)39:2<360::aid-anie360>3.0.co;2-9 · 被引用次数：57 · 研究领域：Catalytic C–H Functionalization Methods、Catalytic Cross-Coupling Reactions、Catalytic Alkyne Reactions

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.