Photocatalytic C−H Functionalization of Nitrogen Heterocycles Mediated by a Redox Active Protecting Group
Marianela G. Pizzio, Ernesto G. Mata, Philippe Dauban, Tanguy Saget
Abstract
Abstract Herein, we report a photocatalytic strategy for the C−H functionalization of saturated azaheterocycles under mild conditions with only one equivalent of starting material. Our strategy is based on a redox active benzamide protecting group that is activated via a halogen‐atom transfer (XAT) process to trigger the formation of an α‐amino radical. This nucleophilic radical intermediate was then engaged in Giese additions and radical cross couplings to afford C−H alkylated and arylated products.
Topics & Concepts
ChemistryBenzamideSurface modificationRedoxPhotoredox catalysisPhotocatalysisNucleophileProtecting groupCombinatorial chemistryAlkylationHalogenPhotochemistryOrganic chemistryCatalysisAlkylPhysical chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques