Photoredox-Catalyzed Alkynylation of C(sp<sup>3</sup>)-H Bonds Adjacent to a Nitrogen Atom of Tertiary Amines with Alkynyl Bromides
A novel and robust alkynylation of C(sp<sup>3</sup>)-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 <i>N</i>-arylamines and <i>N</i>-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.
Authors
- Shenghu Yan
- Guigen Li (ORCID: https://orcid.org/0000-0002-9312-412X)
- Yue Zhang (ORCID: https://orcid.org/0000-0003-2181-7266)
- Tao Wang (ORCID: https://orcid.org/0000-0002-5887-534X)
- Jia‐Yin Wang (ORCID: https://orcid.org/0009-0002-3696-8657)
- Hao Yan (ORCID: https://orcid.org/0009-0008-6171-1080)
- Jin‐Long Dai
Institutions
- Texas Tech University (US)
- China National Petroleum and Chemical Planning Institute (CN)
- Changzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-12
- DOI
- https://doi.org/10.1021/acs.joc.4c02065
- Citations
- 9
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.25
Funders
- Changzhou University
- Natural Science Research of Jiangsu Higher Education Institutions of China