Scalable, Electrochemical Oxidation of Unactivated C–H Bonds

A practical electrochemical oxidation of unactivated C–H bonds is presented. This reaction utilizes a simple redox mediator, quinuclidine, with inexpensive carbon and nickel electrodes to selectively functionalize “deep-seated” methylene and methine moieties. The process exhibits a broad scope and good functional group compatibility. The scalability, as illustrated by a 50 g scale oxidation of sclareolide, bodes well for immediate and widespread adoption.

本研究报道了一种针对未活化碳氢键（C–H bonds）的实用电化学氧化方法。该反应采用廉价易得的碳电极与镍电极，以简单的氧化还原介质（redox mediator）奎宁环（quinuclidine）为媒介，可选择性地对“深埋型”亚甲基与次甲基基团进行官能团化修饰。该方法具备宽泛的底物适用范围与优异的官能团兼容性。以香紫苏内酯（sclareolide）的50克级规模氧化反应为例，其可放大性表现突出，有望实现快速推广与大规模应用。