Anion-Driven C-F Bond Activation of Trifluoromethyl N -Aryl Hydrazones: Application to the Synthesis of 1,3,4-Oxadiazoles.

The CF 3 group attached to N -aryl hydrazone could be activated upon treatment with a suitable base, thus serving as an excellent C1 unit for the assembly of a series of 1,3,4-oxadiazoles by reaction with hydrazides. The transformation is proposed to proceed via the intermediate formation of a gem -difluorinated azoalkene. Furthermore, this reaction features simple conditions and a broad substrate scope with respect to both trifluoromethyl N -aryl hydrazones and hydrazides.