Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Chemistry. 2021 Feb 19;27(11):3682-3687. doi: 10.1002/chem.202005158. Epub 2021 Jan 25.
A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.
本文报道了一种温和、绿色的电氧化方法，可将芳基甲基和醇构建成芳香酯。重要的是，该反应无需使用金属、化学氧化剂、碱、酸，且在室温下进行。此外，研究发现电解质的设计对于偶联产物的氧化态和结构至关重要，这是一种很少有文献报道的效应。这种电氧化偶联过程还对许多脆弱易氧化的官能团如羟基、醛基、烯烃、炔烃以及邻位苄基具有出色的容忍性。此外，一些手性醇的对映体富集在电氧化偶联反应中也得以保留，因此总体而言，这是一种很有前途的合成工具。
