Catalyst- and Additive-Free Electrochemical CO 2 Fixation into Morita-Baylis-Hillman Acetates

The electrochemical carboxylation of Morita-Baylis-Hillman (MBH) acetates with CO2 is presented. The process proceeds in the absence of transition-metal catalysts and relies on the cathodic reduction of MBH acetates to generate nucleophilic anions that are able to trap low-pressure CO2. Valuable succinate derivatives are obtained (20 examples) in high yields (up to 90%) and with excellent functional group tolerance. A remarkable substrate-controlled (electronic nature) regioselectivity of the transformation is documented along with a mechanistic rationale based on control experiments.

Automated summary

This study presents the electrochemical carboxylation of Morita-Baylis-Hillman (MBH) acetates with CO2. The reaction occurs without the need for transition-metal catalysts and involves the cathodic reduction of MBH acetates to generate nucleophilic anions capable of trapping low-pressure CO2. Valuable succinate derivatives are obtained (20 examples) with high yields (up to 90%) and excellent functional group tolerance. The remarkable substrate-controlled (electronic nature) regioselectivity of the reaction is documented, and a mechanistic rationale is proposed based on control experiments.