Visible-Light-Induced α,γ-C(sp<sup>3</sup>)–H Difunctionalization of Piperidines
Biao Wang, Min‐Jie Zhou, Qi‐Lin Zhou
Abstract
Herein, we describe a novel protocol for visible-light-induced α,γ-C(sp3)–H difunctionalization of piperidines. This redox-neutral, atom-economical protocol, which exhibits a broad substrate scope and good functional group compatibility, constitutes a concise, practical method for constructing piperidine-containing bridged-ring molecules. Preliminary mechanistic studies indicated that highly regioselective activation of the inert γ-C(sp3)–H bond of piperidines was achieved through a 1,5-hydrogen atom transfer reaction of a nitrogen radical generated in situ.
Topics & Concepts
ChemistryPiperidineNitrogen atomMoleculeRegioselectivityRing (chemistry)Hydrogen atomPhotochemistryInertFunctional groupCombinatorial chemistryStereochemistryGroup (periodic table)Organic chemistryCatalysisPolymerCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques