Copper‐mediated simple and direct aerobic oxidative esterification of arylacetonitriles with alcohols/phenols

Abstract

A simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved in the presence of a copper salt and molecular oxygen, which produces a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, which allows the oxygenation of C H bond, cleavage of inert C C bond, and formation of C O bond in one pot without the assistance of any of the acids, bases, ligands, and so on. The reaction provides a simple, direct, and efficient protocol towards functionalized esters, especially aryl benzoates, from readily available starting materials.

Synthesis of N-Heteroarenemethyl Esters via C–C Bond Cleavage of Acyl Cyanides Under Transition Metal-Free Conditions

“…Recently, a simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved in the presence of a copper salt and molecular oxygen (Dong et al, 2021). On the other hand, Song and Plietker groups reported aerobic oxidative C-CN bond cleavage of arylacetonitriles leading to various esters with catalysis of Fe and Ru, respectively (Scheme 1C) (Kong et al, 2016;Eisele et al, 2019).…”