Litcius/Paper detail

Direct and Selective Electrocarboxylation of Styrene Oxides with CO<sub>2</sub> for Accessing <i>β</i>‐Hydroxy Acids

Ke Zhang, Bai‐Hao Ren, Xiaofei Liu, Linlin Wang, Min Zhang, Wei‐Min Ren, Xiao‐Bing Lu, Wen‐Zhen Zhang

2022Angewandte Chemie International Edition79 citationsDOI

Abstract

Abstract Highly selective and direct electroreductive ring‐opening carboxylation of epoxides with CO 2 in an undivided cell is reported. This reaction shows broad substrate scopes within styrene oxides under mild conditions, providing practical and scalable access to important synthetic intermediate β ‐hydroxy acids. Mechanistic studies show that CO 2 functions not only as a carboxylative reagent in this reaction but also as a promoter to enable efficient and chemoselective transformation of epoxides under additive‐free electrochemical conditions. Cathodically generated α ‐radical and α ‐carbanion intermediates lead to the regioselective formation of α ‐carboxylation products.

Topics & Concepts

StyreneChemistryCatalysisMaterials scienceOrganic chemistryCopolymerPolymerCarbon dioxide utilization in catalysisCO2 Reduction Techniques and CatalystsRadical Photochemical Reactions