Nucleophilic Organocatalyst for Photochemical Carbon Radical Generation via SN2 Substitution

Photochemical generation of radicals is a powerful way to construct various molecules. But most of these methods rely on initiators or the redox properties of radical precursors. Herein, we report a photochemical organic catalyst that reacts with benzyl halide to generate carbon radical via an SN2 pathway. This nucleophilic catalyst can be easily prepared and is bench-stable. The SN2 process does not rely on the redox properties of halides, showing potential synthetic utility. Control experiments and UV–vis spectroscopic analysis indicate that the SN2 substitution adduct is the key intermediate.