Efficient and general one-pot trifluoromethylative functionalization of amides has been accomplished for the synthesis of various trifluoromethylated bis(indolyl)arylmethane, utilizing trifluoromethyltrimethylsilane and substituted indoles as nucleophiles. The developed reaction involves the in situ generation and trapping of a trifluoromethylated iminium ion, derived from the trifluoromethylated hemiaminal of amide, with various substituted indoles. This method has been successfully extended to the synthesis of diverse trifluoromethylated triarylmethanes employing phenols as nucleophiles. Furthermore, the potential of the method was demonstrated via the two-step synthesis of a trifluoromethylated analog of a hypolipidemic and anti-obesity agent. © 2017 American Chemical Society.