Direct and Selective Electrocarboxylation of Styrene Oxides with CO2 for Accessing β‐Hydroxy Acids

Highly selective and direct electroreductive ring‐opening carboxylation of epoxides with CO2 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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-09, Vol.61 (38), p.e202207660-n/a
Main Authors: Zhang, Ke, Ren, Bai‐Hao, Liu, Xiao‐Fei, Wang, Lin‐Lin, Zhang, Min, Ren, Wei‐Min, Lu, Xiao‐Bing, Zhang, Wen‐Zhen
Format: Article
Language:English
Subjects:
Carbon dioxide
Carbon Dioxide Fixation
Carboxylation
Electrochemistry
Epoxides
Hydroxy Acids
Intermediates
Organic Electrosynthesis
Oxides
Reagents
Styrene
Styrenes
Substrates
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Summary:Highly selective and direct electroreductive ring‐opening carboxylation of epoxides with CO2 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 CO2 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. Highly selective and direct electroreductive ring‐opening carboxylation of epoxides with CO2 in an undivided cell to yield synthetically important β‐hydroxy acids is described. CO2 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202207660