Dialkylzinc‐Mediated Cross‐Coupling Reactions of Perfluoroalkyl and Perfluoroaryl Halides with Aryl Halides |
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Authors: | Hisano Kato Dr. Keiichi Hirano Daisuke Kurauchi Naoyuki Toriumi Prof. Dr. Masanobu Uchiyama |
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Affiliation: | 1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7‐3‐1 Hongo, Bunkyo‐ku, Tokyo 113‐0033 (Japan);2. Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, and Elements Chemistry Laboratory RIKEN, 2‐1 Hirosawa, Wako‐shi, Saitama 351‐0198 (Japan) |
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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. |
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Keywords: | arylation cross‐coupling density functional calculations organozinc reagents perfluoroalkylation |
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