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.