Manganese corrole catalyzed selective oxidation of styrene to benzaldehyde: sodium nitrite functions as an oxidant and cocatalyst?

Organic & Biomolecular Chemistry Pub Date: 2022-09-20 DOI: 10.1039/D2OB01428A

Abstract

Catalytic oxidation using manganese corrole is a hot topic of contemporary porphyrin chemistry, in which PhIO, TBHP, PhI(OAc)2, KHSO5 and m-CPBA are usually used as oxidants. This article reports the first selective oxidation of styrene to benzaldehyde using a manganese(III) corrole catalyst and sodium nitrite (NaNO2) as oxidant and cocatalyst at room temperature. The yield was 158.1% in air and 96.5% under a nitrogen atmosphere, showing oxygen might be involved in the reaction and that NaNO2 is an oxygen source and cocatalyst in the system. The peripheral electron-withdrawing substituents of the manganese corrole were favorable to the catalytic reaction. Radical inhibition and H218O experiments proved that the catalytic reaction was a free radical and hydrolysis-involved reaction.

Graphical abstract: Manganese corrole catalyzed selective oxidation of styrene to benzaldehyde: sodium nitrite functions as an oxidant and cocatalyst
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