Synthesis of fluorinated triazole and isoxazole derivatives by electrochemical fluorination

Abstract

Partially fluorinated triazole derivatives were synthesized through anodic fluorination of alkynes having arylthio group and following Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) with benzyl azide. The other route toward the fluorinated triazoles, namely the anodic fluorination of triazole derivatives once prepared by advanced CuAAC of the alkyne and azide above was also investigated. It was shown that these two routes are mutually complementary methodology for the synthesis of new mono- and difluoromethyltriazole derivatives. Furthermore, Cu(I)-catalyzed isoxazole synthesis from fluorinated alkynes and imidoyl chloride was demonstrated.