Visible-Light-Induced Three-Component Selenofunctionalization of Alkenes: An Aerobic Selenol Oxidation Approach

A photocatalyst-free visible-light-induced selenofunctionalization of alkenes has been developed using a variety of nucleophiles. The homolytic scission of diselenides under visible-light conditions coupled with the aerobic selenol oxidation to diselenides allowed the successful implementation of three-component selenofunctionalization under visible-light irradiation in open-air conditions. The mechanistic studies revealed the critical role of oxygen content in a reaction medium, where the electron transfer process from the carbon-based radicals to either molecular oxygen or selenyl radicals was controlled.本研究开发出一类无需光催化剂的可见光诱导烯烃硒官能化反应（selenofunctionalization），可采用多种亲核试剂（nucleophiles）参与反应。二硒醚（diselenides）在可见光条件下发生均裂（homolytic scission），该过程与需氧条件下硒醇氧化生成二硒醚的反应相耦合，使得三组分硒官能化反应可在敞口空气环境的可见光照射下顺利实现。机理研究揭示了反应介质中氧含量的关键作用：体系内碳中心自由基（carbon-based radicals）向分子氧（molecular oxygen）或硒基自由基（selenyl radicals）的电子转移过程受到精准调控。