A novel method for introducing a polyfluoroalkyl group into aromatic compounds

Introduction of a polyfluoroalkyl group into aromatic compounds was achieved by Friedel-Crafts reaction using (1-chloro-1-hydroperfluoroalkyl) sulfides 1, and the subsequent desulfurizing–difluorination of the resulting product using IF5/Et3N-nHF. Perfluoroethyl, 1,1,2,2,3,3-hexafluoropropyl, and 1,1,2,2,3,3,4,4,5,5-decafluoropentyl groups were introduced to various aromatic compounds by this method. Selective perfluoroethylation of uracil at the 5-position was also performed.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Perfluoroethyl, hexafluoropropyl, and decafluoropentyl groups were introduced to various aromatic compounds. ► Starting material can be prepared from commercially available alcohols. ► Perfluoroethyl group was selectively introduced at the 5-position of uracil using our method.