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.本研究展示了一种可见光诱导、硒自由基介导的芳基炔酸酯多米诺反应，可用于合成1,1-二硒代烯烃衍生物与含硒α,β-不饱和羧酸。该反应条件温和、无金属参与、操作简便且可规模化放大。通过使用催化量的伊红Y（Eosin Y）染料与碳酸铯作为碱，可对脱羧步骤进行精准调控。该方法具备良好的官能团兼容性，产物收率可观。此外，通过制备烯丙醇、α,β-不饱和酯及乙烯基卤化物，进一步拓展了该合成策略的应用价值。