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

The CF3 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.