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

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.