Photoredox-Catalyzed Alkynylation of C(sp3)-H Bonds Adjacent to a Nitrogen Atom of Tertiary Amines with Alkynyl Bromides

A novel and robust alkynylation of C(sp3)–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.