Organocatalyzed Anodic Oxidation of Aldehydes

被引：145
|
作者：
Finney, Eric E. [1 ]
Ogawa, Kelli A. [1 ]
Boydston, Andrew J. [1 ]
机构：
[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 30期
关键词：
OLEFIN COUPLING REACTIONS; INTERNAL REDOX REACTION; ONE-POT SYNTHESIS; ELECTROCHEMICAL OXIDATION; CATALYZED OXIDATIONS; UMPOLUNG REACTIONS; SATURATED ESTERS; CONVERSION; INTERMEDIATE; CARBOXYLATES;
D O I：
10.1021/ja304716r
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A method for the catalytic formation of electroauxiliaries and subsequent anodic oxidation has been developed. The process interfaces N-heterocyclic carbene-based organocatalysis with electro-organic synthesis to achieve direct oxidation of catalytically generated electroactive intermediates. We demonstrate the applicability of this method as a one-pot conversion of aldehydes to esters for a broad range of aldehyde and alcohol substrates. Furthermore, the anodic oxidation reactions are very clean, producing only H-2 gas as a result of cathodic reduction.
引用
收藏
页码：12374 / 12377
页数：4
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