Manganese(III) 5,15-diazaporphyrins: Synthesis, properties, and catalytic use for benzylic C–H fluorination

Abstract

Fluorination of sp3 C–H bonds has attracted considerable attention as a promising method for the synthesis of organofluorine compounds. Manganese porphyrins have been extensively investigated as catalysts in the fluorination of saturated sp3 C–H bonds. Recently, we have found that iron(III) 5,15-diazaporphyrins, which are porphyrin analogues with imine-type sp2-hybridized nitrogen atoms at the meso-positions, showed high catalytic performance in the oxidation of sp3 C–H bonds. Here we disclose the synthesis, structure, and electronic properties of manganese(III) 5,15-diazaporphyrins. We also demonstrate the catalysis of chloromanganese(III) 5,15-diazaporphyrins for benzylic fluorination.