title: Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.
abstract: We report herein that potassium alkyltrifluoroborates can be utilized in oxidative Heck-type reactions with vinyl arenes. The reaction is catalyzed by a Cu(OTf)2/1,10-phenanthroline with MnO2 as the stoichiometric oxidant. In addition to the alkyl Heck, amination, esterification, and dimerization reactions of alkyltrifluoroborates are demonstrated under analogous reaction conditions. Evidence for an alkyl radical intermediate is presented.
authors.affiliation: Department of Chemistry, The State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Timothy W
authors.initials: TW
authors.lastname: Liwosz
authors.forename: Sherry R
authors.initials: SR
authors.lastname: Chemler
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001881:Borates; D003300:Copper