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Published on: November 9, 2019
Electroreductive Carboxylation of Propargylic Acetates with CO2: Access to Tetrasubstituted 2,3-Allenoates
Jing-Hao Qin1, Zhi-Qiang Xiong1, Chaozhihui Cheng1,2
1Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China.
Abstract:
An electroreductive carboxylation of propargylic alcohols with CO2 and then workup with TMSCHN2 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 CO2 radical anion or the 3-aryl propargylic acetate radical anion based on the electron nature of the aryl rings.
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