One-Pot Trifluoromethylative Functionalization of Amides: Synthesis of Trifluoro­methylated Bis(indolyl)­aryl­methanes and Triaryl­methanes

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.