Radical Cascade Reaction of Aryl Alkynoates at Room Temperature: Synthesis of Fully Substituted α,β-Unsaturated Acids with Chalcogen Functionality.

Abstract

A radical-based cascade reaction has been devised for oxidative difunctionalization of aryl alkynoates at room temperature to access stereodefined fully substituted α,β-unsaturated acids bearing a chalcogen functionality in high yields (up to 95%). The protocol is operationally simple, metal-free, scalable, and suppresses the usual CO2 exclusion phenomenon. The utility of this method was showcased in the synthesis of vinyl halides, vinyl selenides, and 3,3-disubstituted indanones.