Tris(pentafluorophenyl)borane has been found to catalyze the two-fold C(sp3 )-H silylation of various trialkylamine derivatives with dihydrosilanes, furnishing the corresponding 4-silapiperidines in decent yields. The multi-step reaction cascade involves amine-to-enamine dehydrogenation at two alkyl residues and two electrophilic silylation reactions of those enamines, one inter- and one intramolecular.
Keywords: C−H activation; Si−H activation; amines; boron; silicon.
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