title: A chemoselective reduction of alkynes to (E)-alkenes.
abstract: The trans reduction of all types of alkynes to give (E)-olefins is achieved through a two-stage trans hydrosilylation and protodesilylation. Reaction of an alkyne and a silane with the ruthenium catalyst [Cp*Ru(MeCN)3]PF6 results in clean hydrosilylation to give only the (Z)-trans addition product at ambient temperature with catalyst loadings of 1-5 mol %. The crude vinylsilane products are then protodesilylated by the action of cuprous iodide and TBAF at rt-35 degrees C. The reaction is compatible with many sensitive functional groups and provides a general trans-alkyne reduction not possible by other means.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Zachary T
authors.initials: ZT
authors.lastname: Ball
authors.forename: Thomas
authors.initials: T
authors.lastname: Jöge
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000475:Alkenes; D000480:Alkynes