Nickel-Catalyzed Umpolung Allylation of Imines with Allylic Alcohols
A nickel-catalyzed allylation of imines, including cyclic imines such as dibenzoxazepines, quinazolinones, and quinoxalin-2(1<i>H</i>)-ones and linear imines, using allylic alcohols as pro-nucleophiles has been developed. This transformation affords homoallylic amines in good to excellent yields with high levels of regio- and diastereoselectivity. Mechanistic studies suggest that the bis(π-allyl)nickel(II) intermediate serves as a crucial intermediate in the catalytic cycle, exhibiting nucleophilic reactivity through its η<sup>1</sup>,η<sup>3</sup> coordination mode.
Authors
- Yuanhong Liu (ORCID: https://orcid.org/0000-0003-1153-5695)
- Xin Xie (ORCID: https://orcid.org/0000-0003-2159-7996)
- Peizhuo Lv (ORCID: https://orcid.org/0000-0002-2671-4314)
- Qiting Wu (ORCID: https://orcid.org/0000-0002-5330-2040)
- Kuo Yuan
Institutions
- East China University of Science and Technology (CN)
- Henan University of Technology (CN)
- Zhengzhou University (CN)
- Henan Academy of Sciences (CN)
- Zhengzhou University of Science and Technology (CN)
- Shanghai Institute of Organic Chemistry (CN)
- New Technology (Israel) (IL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-26
- DOI
- https://doi.org/10.1021/acs.orglett.5c02444
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- National Key Research and Development Program of China