title: (Z)- or (E)-Selective hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: route to either isomer of β-trifluoromethylstyrenes.
abstract: A Pd-catalyzed hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate providing either the (Z)- or (E)-isomer of the vinylborate in >98% purity is described. The initially formed (Z)-isomer of the alkene is transformed to the (E)-isomer with time, irrespective of the catalyst used; coupling with bromo- and iodoarenes provides a variety of (Z)- or (E)-β-trifluoromethylstyrenes. Also, a safe synthesis of the alkynyltrifluoroborate from HFC-245fa and BF3·OEt2 has been described.
authors.affiliation: Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: P Veeraraghavan
authors.initials: PV
authors.lastname: Ramachandran
authors.forename: Wataru
authors.initials: W
authors.lastname: Mitsuhashi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001881:Borates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007536:Isomerism; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000475:Alkenes; D001881:Borates; D006845:Hydrocarbons, Fluorinated; D006846:Hydrocarbons, Halogenated; D013343:Styrenes; C000601271:potassium(3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate; D010165:Palladium