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- Title
Dialkylzinc-Mediated Cross-Coupling Reactions of Perfluoroalkyl and Perfluoroaryl Halides with Aryl Halides.
- Authors
Kato, Hisano; Hirano, Keiichi; Kurauchi, Daisuke; Toriumi, Naoyuki; Uchiyama, Masanobu
- 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.
- Subjects
DIALKYLZINC; ARYL halides; COPPER catalysts; DENSITY functional theory; PHENANTHROLINE; PHTHALOCYANINES
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 10, p3895
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201406292