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通过成对电解与镍催化相结合实现羧酸与芳基卤化物的酯化反应。

Esterification of Carboxylic Acids with Aryl Halides via the Merger of Paired Electrolysis and Nickel Catalysis.

作者信息

Wei Lei, Wang Zhen-Hua, Jiao Ke-Jin, Liu Dong, Ma Cong, Fang Ping, Mei Tian-Sheng

机构信息

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

出版信息

J Org Chem. 2021 Nov 19;86(22):15906-15913. doi: 10.1021/acs.joc.1c00204. Epub 2021 Mar 26.

Abstract

Electrochemistry has been successfully applied in metal catalysis to avoid the usage of chemical redox agents. This strategy proved to be a powerful approach to construct carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds. However, most of the developed methods are based on either anodic oxidation or cathodic reduction, in which a sacrificial reaction occurs at the counter electrode. Paired electrolysis merging with metal catalysis is underdeveloped, wherein both anodic and cathodic processes are taking place simultaneously. Herein, we demonstrated that by using esterification of carboxylic acids with aryl halides via paired electrolysis using nickel as the catalyst the respective aryl esters were obtained in good to excellent yields at room temperature in an undivided electrochemical cell.

摘要

电化学已成功应用于金属催化,以避免使用化学氧化还原试剂。该策略被证明是构建碳-碳(C-C)键和碳-杂原子(C-X)键的有效方法。然而,大多数已开发的方法要么基于阳极氧化,要么基于阴极还原,其中在对电极上会发生牺牲反应。与金属催化相结合的成对电解尚未得到充分发展,在此过程中,阳极和阴极过程同时发生。在此,我们证明,通过使用镍作为催化剂,在未分隔的电化学池中通过成对电解使羧酸与芳基卤化物进行酯化反应,可在室温下以良好至优异的产率得到相应的芳基酯。

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