Photoinduced P–Se Bond Cleavage of Diselenophosphinic Esters: En Route to Selenoethers and Phosphine Selenides
Abstract
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 N 2 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.
Fields of Study & Subjects
Radical Photochemical Reactions
Advanced Polymer Synthesis and Characterization
Organometallic Complex Synthesis and Catalysis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 9
- Pages
- 2977–2984
- Publication date
- 19 February 2026
- Language
- EN