Organic letters

Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts

S Chen, MS Hossain, FW Foss Jr

Index: Chen, Shuai; Hossain, Mohammad S.; Foss, Frank W. Organic Letters, 2012 , vol. 14, # 11 p. 2806 - 2809

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Citation Number: 31

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 ...

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