Copper-Catalyzed Diastereoselective Borylative α-(<i>N</i>-Aryl)aminoalkylation of Vinyl Arenes with Nitrones
A copper-catalyzed three-component coupling of vinyl arenes, bis(pinacolato)diboron, and nitrones has been developed, which offers access to a diverse range of γ-(<i>N</i>-aryl)amino boronates via reductive workup, exhibiting good-to-excellent diastereoselectivities. This new protocol, which can be performed at a gram scale, utilizes nitrones as simple precursors and provides γ-amino boronates having versatile utilities in downstream applications. Additionally, oxidative pathway control allows the selective generation of 3-substituted α,β-unsaturated imines, expanding the synthetic utility of this catalytic system.
Authors
- Shuxia Wang
- Zhen Qin (ORCID: https://orcid.org/0000-0002-8134-4301)
- Xiulian Zhang (ORCID: https://orcid.org/0000-0003-1418-2864)
- Wei Dong (ORCID: https://orcid.org/0000-0001-7759-3981)
- Zixin Ye
- Long Chen (ORCID: https://orcid.org/0000-0001-5908-266X)
- Ming Li (ORCID: https://orcid.org/0000-0003-4906-936X)
- Jingyu Li (ORCID: https://orcid.org/0000-0001-9350-5873)
- Zheng Dang (ORCID: https://orcid.org/0000-0003-3841-7912)
- Chuanzhou Tao (ORCID: https://orcid.org/0000-0002-2297-8726)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-07-16
- DOI
- https://doi.org/10.1021/acs.joc.5c00845
- Citations
- 2
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Jiangsu Ocean University
- Natural Science Research of Jiangsu Higher Education Institutions of China