title: Palladium-catalyzed cross-coupling of sterically demanding boronic acids with α-bromocarbonyl compounds.
abstract: A catalyst system generated in situ from Pd(dba)(2) and tri(o-tolyl)phosphine mediates the coupling of arylboronic acids with alkyl α-bromoacetates under formation of arylacetic acid esters at unprecedented low loadings. The new protocol, which involves potassium fluoride as the base and catalytic amounts of benzyltriethylammonium bromide as a phase transfer catalyst, is uniquely effective for the synthesis of sterically demanding arylacetic acid derivatives.
authors.affiliation: Department of Organic Chemistry, Technische Universität Kaiserslautern, Erwin-Schroedinger-Str. Geb. 54, 67663 Kaiserslautern, Germany.
authors.forename: Bettina
authors.initials: B
authors.lastname: Zimmermann
authors.forename: Wojciech I
authors.initials: WI
authors.lastname: Dzik
authors.forename: Thomas
authors.initials: T
authors.lastname: Himmler
authors.forename: Lukas J
authors.initials: LJ
authors.lastname: Goossen
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D007659:Ketones; D010165:Palladium; D001966:Bromine