Radical Cyanotrifluoromethylation of Isocyanides: Step-Economical Access to CF3-Containing Nitriles, Amines, and Imines

A novel copper-catalyzed radical cyanotrifluoromethylation has been achieved through a multicomponent reaction of isocyanides, Togni's reagent, and trimethylsilyl cyanides, affording trifluoroacetimidoyl nitriles in good yields. This reaction demonstrates a unique feature of merging two valuable functional groups trifluoromethyl (CF3) and cyan (CN)-onto the same C atom. The transformation proceeds by the initial addition of the CF3 radical to isocyanide and the subsequent intermolecular C-CN formation. The products can be successfully transformed to a series of CF3-containing amines and imines that may serve in the synthesis of valuable pharmaceuticals and agrochemicals.