Litcius/Paper detail

Photocatalytic direct borylation of carboxylic acids

Qiang Wei, Yuhsuan Lee, Weiqiu Liang, Xiaolei Chen, Bo‐Shuai Mu, Xi‐Yang Cui, Wangsuo Wu, Shuming Bai, Zhibo Liu

2022Nature Communications39 citationsDOIOpen Access PDF

Abstract

Abstract The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent derivatives above 150 °C reaction temperature. Here, we report a direct decarboxylative borylation method of carboxylic acids enabled by visible-light catalysis and that does not require any extra stoichiometric additives or synthesis steps. This operationally simple process produces CO 2 and proceeds under mild reaction conditions, in terms of high step economy and good functional group compatibility. A guanidine-based biomimetic active decarboxylative mechanism is proposed and rationalized by mechanistic studies. The methodology reported herein should see broad application extending beyond borylation.

Topics & Concepts

BorylationChemistryCarboxylic acidPhotocatalysisCombinatorial chemistryCatalysisGuanidineCovalent bondOrganic chemistryArylAlkylOrganoboron and organosilicon chemistryCarbon dioxide utilization in catalysisCatalytic C–H Functionalization Methods