Biomimetic Oxidation of Diphenyl Sulfide with Metalloporphyrin-O_2-NaBH_4 System

概要

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A P-450 model system consisting of metallo-meso-tetraphenylporphyrins, O_2 and NaBH_4 in basic solution is described. It has three remarkable features; 1) dioxygen is activated on a metalloporphyrin; 2) the reductant is used effectively, i.e., the efficiency of the reductant, calculated on the assumption that two electrons are consumed to produce an active-two-electron oxidant in the catalytic cycle, is 37%; 3) the life of the catalyst is extremely long for a P-450 model system. The maximum turnover is 336.When meso-tetraphenylporphyrinatomanganese(III) chloride (1) was used as a catalyst in this system, diphenyl sulfide was oxidized stepwise to diphenyl sulfoxide an then to diphenylsulfone. When meso-tetraphenylporphyrinatoiron(III) chloride (2) was used as a catalyst, diphenyl sulfide was oxidized quantitatively to diphenyl sulfoxide.
公益社団法人日本薬学会の論文
1993-08-15