Electroreductive Carboxylation of Propargylic Acetates with CO<sub>2</sub>: Access to Tetrasubstituted 2,3-Allenoates
Jing‐Hao Qin, Zhiqiang Xiong, Chaozhihui Cheng, Ming Hu, Jin‐Heng Li
Abstract
An electroreductive carboxylation of propargylic alcohols with CO 2 and then workup with TMSCHN 2 to construct tetrasubstituted 2,3-allenoates is developed. This method allows the incorporation of an external ester group into the resulting allene system through electroreduction, carboxylation, and deacetoxylation cascades. Mechanistically, electricity on/off experiments and cyclic voltammetry analysis support the preferential generation of the CO 2 radical anion or the 3-aryl propargylic acetate radical anion based on the electron nature of the aryl rings.
Topics & Concepts
CarboxylationChemistryAlleneArylCyclic voltammetryAcetonitrileMedicinal chemistryIonCombinatorial chemistryOrganic chemistryElectrochemistryCatalysisElectrodeAlkylPhysical chemistryCO2 Reduction Techniques and CatalystsCarbon dioxide utilization in catalysisCatalytic C–H Functionalization Methods