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

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.