Radical Coupling Initiated by Organophosphine Addition to Ynoates
Jing Cao, Antonia Seitz, José A. Forni, Anastasios Polyzos, David W. Lupton
Abstract
Dual nucleophilic phosphine photoredox catalysis is yet to be developed due to facile oxidation of the phosphine organocatalyst to the phosphoranyl radical cation. Herein, we report a reaction design that avoids this event and exploits traditional nucleophilic phosphine organocatalysis with photoredox catalysis to allow the Giese coupling with ynoates. The approach has good generality, while its mechanism is supported by cyclic voltametric, Stern-Volmer quenching, and interception studies.
Topics & Concepts
Coupling (piping)Political scienceChemistryMaterials scienceComposite materialRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods