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
收藏
页码：2806 / 2809
页数：4
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