Organic Letters 2012-06-01

Organocatalytic Dakin oxidation by nucleophilic flavin catalysts.

Shuai Chen, Mohammad S Hossain, Frank W Foss

Index: Org. Lett. 14(11) , 2806-9, (2012)

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Abstract

Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.