Diselenide-enabled photocatalytic hydroazolation of gem-difluoroalkenes

Abstract

Difluoromethylene-containing molecules and azoles, independently, have wide applications in materials science, pharmaceuticals, agrochemicals and as biological diagnostic probes. However, compounds bearing the N-α,α-difluoroalkyl azole [(azole)N–CF₂R] motif remain scarce in academic and patent literature, presumably due to a lack of synthetic methods. Such compounds could be convergently accessed in a single step via the hydroazolation of gem-difluoroalkenes. However, most existing functionalization reactions of gem-difluoroalkenes proceed through a β-fluoride elimination pathway that generates monofluorinated derivatives. Herein, we report a photocatalytic hydroazolation of gem-difluoroalkenes to generate (azole)N–CF₂R that employs an uncommon diselenide co-catalyst to avoid the defluorinative process, ultimately enabling facile access to underexplored medicinally and agriculturally-relevant chemical space.