Efficient Biomimetic Decarboxylation of Diphenylacetic Acid by [Mn(TPP)X] n -Bu 4 NIO 4 Catalytic Systems: Effect of Anionic Axial Ligands (X

Abstract

Highly efficient decarboxylation of diphenylacetic acid has been performed by tetrabutylammonium periodate in the presence of different [Mn(TPP)X] complexes (X^- = anionic axial ligand) in CH₂Cl₂. In these catalytic systems, diphenylacetic acid was selectively (>97%) converted to benzophenone. The reactivity of manganese porphyrins are markedly influenced by the nature of anionic axial ligands and the efficiency of the catalysts decreases in the order: CN^- > OCN^- > N₃^- > SCN^- > F^- > OAc^- ∼ Cl^- ∼ Br^- ∼ I^-∼ ClO₄^-. Marked improvement in reactivities and selectivities has resulted from addition of imidazole and its derivatives to the reaction mixture. π-Bonding interaction in Mn–X moiety and the possibility of distal hydrogen bonding between imidazole and X^- is presented to describe the enhanced catalytic activities observed for Mn(TPP)X (X^- = SCN^-, N₃^-, OCN^-, CN^-). A simple catalytic cycle is also proposed to show the role of X^- in the possible intermediates.

Keywords

diphenylacetic acid manganese porphyrins anionic ligands decarboxylation catalysis

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Efficient Biomimetic Decarboxylation of Diphenylacetic Acid by [Mn(TPP)X] n -Bu 4 NIO 4 Catalytic Systems: Effect of Anionic Axial Ligands (X - )

Abstract

Keywords

References