Change in the Product Selectivity in the Visible Light-Induced Selenium Radical-Mediated 1,4-Aryl Migration Process

Abstract

Herein, we demonstrate a visible light-induced selenium radical-mediated domino reaction of aryl alkynoates, for the synthesis of 1,1-diselenide alkene derivatives and selenium-containing α,β-unsaturated carboxylic acid. The process is mild, metal free, easy to handle, and scalable. The decarboxylation step can be controlled by applying a catalytic amount of Eosin Y dye and cesium carbonate as a base. The methodology shows good functional group tolerance and provides decent yields of the products. In addition, the synthetic utility of this protocol was expanded further by preparing the allylic alcohol, α,β-unsaturated ester, and vinylic halides.

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