Palladium-Catalyzed Polyfluorophenylation of Porphyrins with Bis(polyfluorophenyl)zinc Reagents

A facile and efficient method for the synthesis of pentafluorophenyl- and related polyfluorophenyl-substituted porphyrins has been achieved via palladium-catalyzed cross-coupling reactions of brominated porphyrins with bis(polyfluorophenyl)zinc reagents. The reaction is applicable to a variety of free-base bromoporphyrins, their metal complexes, and a number of bis(polyfluorophenyl)zinc reagents.