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Paper | Special issue | Vol 88, No. 2, 2014, pp.1201-1212
Published online, 4th October, 2013
DOI: 10.3987/COM-13-S(S)84
Polyfluoroalkylation of Carbonyl Compounds by Polyfluoroalkyl Anions Generated from Polyfluorcarboxamides

Natshumi Wakita and Shoji Hara*

*Graduate School of Engineering, Hokkaido University, Kita 13 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan


Polyfluoroalkyl anions, generated by reduction of (polyfluoroalkanoyl)piperidines with Et3BHK, were used for the polyfluoroalkylation of carbonyl compounds. Trifluoromethylation of aromatic aldehydes proceeded in good yields, and that of aliphatic aldehydes afforded a moderate yield. In contrast, the yield was low when the reaction involved benzophenone. Pentafluoroethylation and octafluorobutylation of aldehydes were also carried out by using the corresponding (polyfluoroalkanoyl)piperidines, which were prepared from commercially available polyfluorocompounds. The (polyfluoroalkanoyl)piperidines were also prepared through polyfluorination, and were used in the polyfluoroalkylation of aldehydes.