title: A Mechanistic Dichotomy Leading to a Ruthenium-Catalyzed cis-Addition for Stereoselective Formation of (Z)-Vinyl Bromides.
abstract: 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.
authors.affiliation: Department of Chemistry, Stanford University Stanford, CA 94305-5080 (USA).
authors.initials: BM
authors.lastname: Trost
authors.initials: AB
authors.lastname: Pinkerton