Trifluoromethylation of non-activated aldimines with trimethyl(trifluoromethyl)silane in the presence of tetramethylammonium fluoride: A closer look into the reaction route

The reactions of non-activated aldimines with trimethyl(trifluoromethyl)si lane and 1 equiv. of tetramethylammonium fluoride proceed via the formation of tetramethylammonium amides which were identified by low-temperature F-19 NMR experiments. Consecutive reactions of the salts formed in situ with electrophiles yielded trifluoromethylated amines. Fluoride elimination is observed in the absence of electrophilic substrates leading to the formation of difluoromethylated ketimines. (C) 2007 Elsevier B.V. All rights reserved.