Electrocarboxylation of <i>N</i>-Acylimines with Carbon Dioxide: Access to Substituted α-Amino Acids
Ke Zhang, Xiaofei Liu, Wen‐Zhen Zhang, Wei‐Min Ren, Xiao‐Bing Lu
Abstract
Direct electrocarboxylation of various N-acylimines with atmospheric CO2 is achieved in an undivided cell under mild conditions, affording substituted α-amino acids in yields of 62–95%. This reaction is conducted with high efficiency using triethanolamine as an external reductant under nonsacrificial anode conditions, and can be facilely performed on gram scale. Preliminary mechanistic studies including cyclic voltammetry and control experiments support N-radical carbanion as the key intermediate.
Topics & Concepts
ChemistryCarbanionTriethanolamineCyclic voltammetryAmino acidAnodeCombinatorial chemistryCarbon dioxideMedicinal chemistryOrganic chemistryElectrodeElectrochemistryBiochemistryPhysical chemistryAnalytical Chemistry (journal)Carbon dioxide utilization in catalysisCO2 Reduction Techniques and CatalystsAsymmetric Hydrogenation and Catalysis