Practical and Efficient Synthesis of Various meso-Functionalized Porphyrins via Simple Ligand-Free Nickel-Catalyzed C−O, C−N, and C−C Cross-Coupling Reactions

Various meso-functionalized porphyrins were conveniently synthesized by direct reactions of meso-bromoporphyrins with oxygen-, nitrogen-, and carbon-based nucleophiles in moderate to high yields via practical, efficient, and ligand-free nickel-catalyzed C-O, C-N, and C-C bond-forming reactions. The central metal ions of the substrate porphyrin have much effect on the reactions. Introduction of Ni(II) as a central metal ion into the substrate porphyrin markedly accelerated the cross-coupling.