Photoredox-Catalyzed 1,4-Peroxidation–Sulfonylation of Enynones: A Three-Component Radical Coupling Approach for the Synthesis of Highly Functionalized Allenes
Divya Bhatt, Kosei Miyake, Shuichi Nakamura, Hun Young Kim, Kyungsoo Oh
Abstract
An Eosin Y-catalyzed visible light-promoted 1,4-peroxidation-sulfonylation of enynones was achieved to give tetrasubstituted allenes. The photoredox catalysis of Eosin Y allowed the concomitant formation of peroxy and sulfonyl radicals, where the preferential peroxy radical addition to the alkene moiety of enynones resulted in the subsequent α-keto radical-sulfonyl radical cross couplings. The developed photoredox catalysis of Eosin Y demonstrates a regioselective 1,4-diradical addition strategy, opening up a new possibility of diradical functionalization of conjugate systems.
Topics & Concepts
ChemistryPhotoredox catalysisSulfonylEosin YRegioselectivityDiradicalRadicalPhotochemistryEosinMoietyAlkeneCatalysisOrganic chemistryPhotocatalysisAlkylStainingExcited statePathologyNuclear physicsPhysicsMedicineSinglet stateSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods