title: Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation.
abstract: A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed. Mechanistically, the reaction proceeds through (1) Suzuki coupling, (2) base-induced fragmentation, and (3) deformylation as shown by characterization of all postulated intermediates. Under optimized conditions (PdCl(2)dppf, KF, DMSO/H(2)O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles with up to 88% yield.
authors.affiliation: Novartis Institutes for Biomedical Research, Forum 1, Novartis Campus, CH-4056 Basel, Switzerland. juraj.velcicky@novartis.com
authors.forename: Juraj
authors.initials: J
authors.lastname: Velcicky
authors.forename: Arne
authors.initials: A
authors.lastname: Soicke
authors.forename: Roland
authors.initials: R
authors.lastname: Steiner
authors.forename: Hans-Günther
authors.initials: HG
authors.lastname: Schmalz
mesh_terms: D000097:Acetonitriles / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D007555:Isoxazoles / Q000737:chemistry*; D008745:Methylation; D010165:Palladium / Q000737:chemistry*
chemical_list: D000097:Acetonitriles; D001897:Boronic Acids; D001965:Bromides; D007555:Isoxazoles; D010165:Palladium; C008756:palladium chloride