Dialkylzinc‐Mediated Cross‐Coupling Reactions of Perfluoroalkyl and Perfluoroaryl Halides with Aryl Halides. Issue 10 (28th January 2015)

• Record Type: Journal Article
• Authors: Kato, Hisano; Hirano, Keiichi; Kurauchi, Daisuke; Toriumi, Naoyuki; Uchiyama, Masanobu
• Is Part Of: Chemistry. Volume 21:Issue 10(2015)
• Page Start: 3895
• Page End: 3900
• Publication Date: 2015-01-28
• Subjects: arylation -- cross‐coupling -- density functional calculations -- organozinc reagents -- perfluoroalkylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201406292
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : RF values : A highly chemoselective perfluoroalkylation of aromatic halides is reported. Thermally stable perfluoroalkylzinc reagents, generated by rapid halogen–zinc exchange between diorganozinc and perfluoroalkyl halide species, couple with a wide range of aryl halides in the presence of copper catalyst, in moderate to high yields. The perfluoroalkylzinc species display good stability, as indicated by DFT calculations.