Dialkylzinc-mediated cross-coupling reactions of perfluoroalkyl and perfluoroaryl halides with aryl halides.
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.
['Kato|Hisano|H|', 'Hirano|Keiichi|K|', 'Kurauchi|Daisuke|D|', 'Toriumi|Naoyuki|N|', 'Uchiyama|Masanobu|M|']
D002384:Catalysis D003432:Cross-Linking Reagents D006219:Halogens D006845:Hydrocarbons, Fluorinated D007202:Indicators and Reagents D015394:Molecular Structure D011789:Quantum Theory D015032:Zinc
cross-coupling perfluoroalkylation arylation density functional calculations organozinc reagents