Photoredox-Catalyzed Alkynylation of C(sp<sup>3</sup>)-H Bonds Adjacent to a Nitrogen Atom of Tertiary Amines with Alkynyl Bromides
Jin‐Long Dai, Tao Wang, Hao Yan, Yue Zhang, Shenghu Yan, Guigen Li, Jia‐Yin Wang
Abstract
A novel and robust alkynylation of C(sp 3 )–H bonds adjacent to a nitrogen atom of tertiary amines with alkynyl bromides as radical alkynylating reagents has been realized under visible-light irradiation. A range variety of tertiary amines including N -arylamines and N -alkylamine have been coupled with both aromatic and aliphatic alkynyl bromides to furnish 51 examples of propargylamines in moderate to excellent yields (31–80% yields). The possible mechanism was a radical addition–elimination process based on preliminary mechanistic studies.
Topics & Concepts
AlkynylationCatalysisNitrogen atomNitrogenChemistryAtom (system on chip)Medicinal chemistryPhotochemistryOrganic chemistryRing (chemistry)Computer scienceEmbedded systemCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques