Manganese corrole catalysts efficiently oxidize organic sulfides into sulfoxides in the presence of a small amount of water using iodobenzene diacetate [PhI(OAc)2] as a mild sacrificial oxidant. Thioanisoles of varying substitutions can be efficiently oxidized with high selectivity for sulfoxides and quantitative conversions up to 2,500 TONs. The effects of the catalyst, including the corrole ligands and oxidation states of the central manganese metal, were investigated and demonstrated that the catalytic sulfoxidations were especially affected. The previously studied manganese(V)-oxo corroles were generated in the oxidation of various thioanisoles and their kinetic activity examined. The results of the competition studies suggest the oxidation states of the manganese metal determine the nature of the active oxidants present during the oxidative process and greatly affect the catalytic activity of the corrole.

Efficient chemoselective oxidations of sulfides catalyzed by manganese corrole with iodobenzene diacetate

2019 Spring National Meeting

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