title: Copper-catalyzed three-component borylstannylation of alkynes.
abstract: Regio- and stereoselective installation of boryl and stannyl moieties into a carbon-carbon triple bond of various alkynes has been achieved based on a three-component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate-tricyclohexylphosphine complex, giving diverse vic-borylstannylalkenes in a straightforward manner. Carbon-tin and carbon-boron bonds of the resulting borylstannylation product are successively transformed into carbon-carbon bonds by a Migita-Kosugi-Stille and a Suzuki-Miyaura coupling, leading to the formation of (Z)-tamoxifen with anti-breast cancer activity.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Takemoto
authors.forename: Hiroto
authors.initials: H
authors.lastname: Yoshida
authors.forename: Ken
authors.initials: K
authors.lastname: Takaki
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001896:Boron Compounds; D009947:Organotin Compounds; D003300:Copper