N-Heterocyclic Carbene Catalyzed Radical Coupling of Aldehydes with Redox-Active Esters

被引：85

作者：

Song, Runjiang ^{[2
]}

Chi, Yonggui Robin ^{[1
,2
]}

机构：

[1] Guizhou Univ, Minist Educ, Key Lab Green Pesticide & Agr Bioengn, Lab Breeding Base Green Pesticide & Agr Bioengn, Guiyang 550025, Guizhou, Peoples R China

[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 26期

基金：

中国国家自然科学基金; 新加坡国家研究基金会;

关键词：

ketones; N-heterocyclic carbenes; radical intermediates; redox-active esters; single-electron-transfer reactions; SINGLE-ELECTRON-TRANSFER; BETA-HYDROXYLATION; ENALS;

D O I：

10.1002/anie.201902792

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Heterocyclic carbene catalyzed radical reactions are challenging and underdeveloped. In a recent study, Ohmiya, Nagao and co-workers found that aldehyde carbonyl carbon centers can be coupled with alkyl radicals under NHC catalysis. An elegant aspect of this study is the use of a redox-active carboxylic ester that behaves as an single-electron oxidant to convert the Breslow intermediate into a radical adduct and concurrently release an alkyl radical intermediate as a reaction partner.

引用

页码：8628 / 8630

页数：3

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