Frustrated Radical Pair‐Initiated Hydrodehalogenation of Alkyl and Aryl Halides under Visible Light

Here we employed Al(C6F5)3/Mes3P frustrated radical pair (FRP) to catalyze hydrodehalogenation reaction. Through the initiation of the FRP, stannane radicals were generated to facilitate the halogen-atom transfer (XAT) process and proceed the hydrodehalogenation of a wide range of alkyl and aryl halides under visible light at room temperature. Electron paramagnetic resonance (EPR) experiment, radical clock reaction coupled with control experiments provide solid evidence to support the radical mechanism. Moreover, this strategy can be applied to the synthesis of pharmaceutical compounds, such as indoles and quinolines as well as the deuterated compounds. The frustrated radical pair (FRP) presents a promising approach for initiating hydrodehalogenation reactions of alkyl and aryl halides. This method utilizes catalytic amounts of Al(C6F5)3/Mes3P FRP, followed by halogen-atom transfer (XAT) of stannane under visible light at room temperature. Noteworthy for its high efficiency, broad substrate scope, mild reaction conditions and capability in deuterium-labeled experiments, this system exhibits potential in pharmaceutical chemistry and contributes to the applicability of FLPs in the field of radical chemistry. image