Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts

被引：66

作者：

Chen, Shuai ^{[1
]}

Hossein, Mohammad S. ^{[1
]}

Foss, Frank W., Jr. ^{[1
]}

机构：

[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 11期

基金：

美国国家科学基金会;

关键词：

BAEYER-VILLIGER OXIDATION; OXYGEN-ATOM TRANSFER; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; ALKYL HYDROPEROXIDES; AROMATIC-ALDEHYDES; CRYSTAL-STRUCTURE; EFFICIENT; AMINES; MONOOXYGENASES;

D O I：

10.1021/ol3010326

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2806 / 2809

页数：4

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