Silylation and (Hetero)aryl/alkenylation of Unactivated Alkenes via Radical-Mediated Distal 1,4-Migration with Hydrosilanes under Organophotocatalysis
Ting Wang, Lu Chen, Yuanyuan Liu, Zhengbing Zhang, Pan Han, Lin‐Hai Jing
Abstract
We report a novel organic photoredox catalysis to achieve unprecedented γ-(hetero)aryl/alkenyl-δ-silyl aliphatic amines via silyl-mediated distal (hetero)aryl/alkenyl migration of aromatic/alkenyl amines bearing unactivated alkenes with hydrosilanes. This protocol features mild and metal-free reaction conditions, high atom economy, excellent selectivity, and functional group compatibility. Mechanistic studies suggest that silylation and (hetero)aryl/alkenylation involve photoredox hydrogen atom transfer catalysis and subsequent 1,4-migration of a remote (hetero)aryl/alkenyl group from nitrogen to carbon.
Topics & Concepts
SilylationChemistryArylCatalysisNitrogen atomPhotoredox catalysisFunctional groupSelectivityMedicinal chemistryCombinatorial chemistryPhotochemistryOrganic chemistryGroup (periodic table)AlkylPhotocatalysisPolymerRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods