title: Dialkylzinc-mediated cross-coupling reactions of perfluoroalkyl and perfluoroaryl halides with aryl halides.
abstract: A highly chemoselective perfluoroalkylation reaction of aromatic halides is reported. Thermally stable perfluoroalkylzinc reagents, generated by a rapid halogen-zinc exchange reaction between diorganozinc and perfluoroalkyl halide species, couple with a wide range of aryl halides in the presence of a copper catalyst, in moderate to high yields. Good stability of the perfluoroalkylzinc species was indicated by DFT calculation and the reagents were storable for at least three months under argon without loss of activity. This method is applicable to gram-scale synthesis, and its functional group tolerance compares favorably with reported protocols.
authors: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan).
authors: Hisano
authors: H
authors: Kato
authors: Keiichi
authors: K
authors: Hirano
authors: Daisuke
authors: D
authors: Kurauchi
authors: Naoyuki
authors: N
authors: Toriumi
authors: Masanobu
authors: M
authors: Uchiyama
mesh_terms: D002384:Catalysis; D003432:Cross-Linking Reagents; D006219:Halogens / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory; D015032:Zinc / Q000737:chemistry*
chemical_list: D003432:Cross-Linking Reagents; D006219:Halogens; D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D015032:Zinc
keywords: arylation; cross-coupling; density functional calculations; organozinc reagents; perfluoroalkylation