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Disclosed herein is a dehydrosilylative difluoroamidation of α-Csp³–H of tetrahydroisoquinolines with α,α-difluoro-α-TMS-acetamides. The process, which occurs at ambient temperature in the absence of any transition metals, provides direct access to a broad range of α,α-difluoroacetamide-substituted tertiary amine derivatives in high yields. Moreover, the method was successfully applied in the Csp³–H-directed difluorophosphorylation and difluorocarboxylation under the same conditions.