Photoinduced P-Se Bond Cleavage of Diselenophosphinic Esters: En Route to Selenoethers and Phosphine Selenides

Diselenophosphinic esters are conventionally employed as RAFT agents in polymerization. Herein, we report the novel photoactivity of diselenophosphinic esters, which can be readily generated in situ from potassium diphenylphosphinodiselenoate and alkyl bromides via an S_N2 substitution. Potassium diphenylphosphinodiselenoate serves as a readily available selenium source. The in situ-generated diselenophosphinic esters undergo homolytic P-Se bond cleavage upon visible-light irradiation to form both selenium- and phosphorus-centered radicals. Subsequently, these radicals are captured by alkenes and converted into selenoethers and phosphine selenides. This protocol demonstrates broad functional group tolerance, enabling the late-stage transformation of complex molecules.