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.

Development of ß,ß-Dibrominated Secondary Enamides and Their Application to the Synthesis of 5-Br Oxazoles.

Herein, we report a base promoted dibromination of enamides using CBr4 as a bromine source to provide expedient access to ß,ß-dibrominated secondary enamides. Preliminary synthetic application study shows that these novel products can be readily transformed to 5-Br oxazoles via Cu(I) catalyzed intramolecular cyclization in good yields.