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

Jin-Long Dai; Tao Wang; Yan Hao; Yue Zhang; Shenghu Yan; Guigen Li; Jia-Yin Wang

doi:10.1021/acs.joc.4c02065

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

J Org Chem. 2024 Oct 12. doi: 10.1021/acs.joc.4c02065. Online ahead of print.

Authors

Jin-Long Dai^{1

2}, Tao Wang^{1

2}, Yan Hao^{1

2}, Yue Zhang^{1

2}, Shenghu Yan^{1

2}, Guigen Li³, Jia-Yin Wang^{1

2}

Affiliations

¹ School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.
² Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.
³ Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409, United States.

PMID: 39395008
DOI: 10.1021/acs.joc.4c02065

Abstract

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.