Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles
Keyuan Zhang, Qi Jiang, Chonglong He, Mingyou Hu, Yangyang Cheng, Xin‐Hua Duan, Le Liu
Abstract
We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methylenecarbocycles but also introduces a new mechanistic pathway with aryl group migration, surpassing the conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.
Topics & Concepts
ChemistrySmiles rearrangementSulfonylEne reactionAlkynePhotoredox catalysisCatalysisArylCascadeVisible spectrumPhotochemistryBroad spectrumCombinatorial chemistryMedicinal chemistryOrganic chemistryPhotocatalysisAlkylPhysicsOptoelectronicsChromatographySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods