N-Heterocyclic Carbene-Catalyzed Oxidative Esterification of Aldehydes: Facile Access to α-Acyloxyacetates and Cyanomethyl Esters

doi:10.6023/cjoc201803040

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 3056-3062.DOI: 10.6023/cjoc201803040 Previous Articles Next Articles

Articles

氮杂环卡宾催化芳香醛的氧化酯化反应

巨磊, 马春梅, 唐蜜, 王妍卉, 虞心红, 马红梅

上海市新药设计重点实验室生物反应器工程国家重点实验室华东理工大学药学院制药工程系上海 200237

收稿日期:2018-03-25 修回日期:2018-06-19 发布日期:2018-07-05
通讯作者: 虞心红, 马红梅 E-mail:xhyu@ecust.edu.cn;hmma@ecust.edu.cn
基金资助:
国家自然科学基金（Nos.20972051，21476078）和市科委（Nos.12431900900，12431900902，08431901800，08430703900）资助项目.

N-Heterocyclic Carbene-Catalyzed Oxidative Esterification of Aldehydes: Facile Access to α-Acyloxyacetates and Cyanomethyl Esters

Ju Lei, Ma Chunmei, Tang Mi, Wang Yanhui, Yu Xinhong, Ma Hongmei

Shanghai Key Laboratory of New Drug Design, State Key Laboratory of Bioengineering Reactors, School of Pharmacy, East China University of Science & Technology, Shanghai 200237

Received:2018-03-25 Revised:2018-06-19 Published:2018-07-05
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20972051, 21476078) and the Science and Technology Commission of Shanghai Municipality (Nos. 12431900900, 12431900902, 08431901800, 08430703900).

1. N-Heterocyclic Carbene-Catalyzed Oxidative Esterification of Aldehydes: Facile Access to α-Acyloxyacetates and Cyanomethyl Esters.PDF(2109KB)

Abstract

An efficient N-heterocyclic carbene-catalyzed oxidative esterification reaction of aldehydes with ethyl bromoacetate or bromoacetonitrile has been explored. This transition metal-free protocol allows access to a wide variety of α-acyloxyacetates and cyanomethyl esters in good to excellent yields under mild reaction condition.

Key words: carbene, aldehydes, esterification, oxidation, organocatalysis

Cite this article

Ju Lei, Ma Chunmei, Tang Mi, Wang Yanhui, Yu Xinhong, Ma Hongmei. N-Heterocyclic Carbene-Catalyzed Oxidative Esterification of Aldehydes: Facile Access to α-Acyloxyacetates and Cyanomethyl Esters[J]. Chin. J. Org. Chem., 2018, 38(11): 3056-3062.

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氮杂环卡宾催化芳香醛的氧化酯化反应

N-Heterocyclic Carbene-Catalyzed Oxidative Esterification of Aldehydes: Facile Access to α-Acyloxyacetates and Cyanomethyl Esters

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