Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds
Hang Chen, Yang Zhou, Panpan Lei, Haifeng Wang, Qiongjiao Yan, Roberta Properzi, Wei Wang, Lin‐Hai Jing, Fen‐Er Chen
Abstract
Visible light-mediated site-specific C(sp3)-H xanthylation of amides has been accomplished using N-xanthylamides. The N-centered radicals generated by light initiation of N-xanthylamide substrates undergo 1,5-hydrogen atom transfer to form benzylic or alkyl radical intermediates under metal- and catalyst-free conditions. This method exhibits a broad substrate scope, high functional group tolerance, and high regioselectivity. Furthermore, this strategy provides straightforward access to a range of derivatives through the subsequent elaboration of the xanthate group.
Topics & Concepts
RegioselectivityIntramolecular forceFunctional groupChemistryXanthateVisible spectrumAlkylRadicalCatalysisSubstrate (aquarium)PhotochemistryHydrogen atomCombinatorial chemistryStereochemistryPolymer chemistryOrganic chemistryMaterials scienceGeologyPolymerOceanographyOptoelectronicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions