Visible-Light-Induced Alkylarylation of Unactivated Alkenes via Radical Addition/Truce–Smiles Rearrangement Cascade
Chonglong He, Keyuan Zhang, Dan‐Ning Wang, Min Wang, Yue-Jie Niu, Xin‐Hua Duan, Le Liu
Abstract
We disclosed a visible-light-induced alkylarylation reaction of unactivated alkenes via a metal-free radical addition/aryl translocation cascade sequence. Distal olefinic sulfonate was designed as a unique molecular scaffold allowing for a domino process to synthesize valuable alkylarylated alcohols in good yields with excellent diastereoselectivity, featuring mild reaction conditions, broad substrate scope, and excellent functional group tolerance. The mechanism investigation suggests that a visible-light-induced radical chain process dominates the cascade transformation.
Topics & Concepts
ChemistryCascade reactionCascadeAryl radicalRadicalFunctional groupArylDominoSulfonateSubstrate (aquarium)PhotochemistryVisible spectrumCombinatorial chemistrySmiles rearrangementStereochemistryOrganic chemistryCatalysisOceanographyOptoelectronicsSodiumAlkylPhysicsChromatographyGeologyPolymerRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques