An electroreductive carboxylation of propargylic alcohols with CO and then workup with TMSCHN 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 radical anion or the 3-aryl propargylic acetate radical anion based on the electron nature of the aryl rings.
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| http://dx.doi.org/10.1021/acs.orglett.3c03735 | DOI Listing |
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