Intra-/Intermolecular 1,2-Diamination of Alkenyl Oximes with <i>O</i>-Benzoylhydroxylamines Enabled by Copper Catalysis
We here describe a versatile, convenient, and efficient approach to synthesize cyclic nitrone compounds by diamination of alkene, which was catalyzed by simple copper salts under basic conditions with good chemoselectivity. The method utilized γ,δ-unsaturated ketoximes with <i>O</i>-benzoylhydroxylamines as an electrophilic nitrogen source to realize intra-/intermolecular 5-<i>exo</i>-trig cyclization of internal alkenes of unsaturated ketoximes without external oxidants required, and a series of substitution patterns, both donor and withdrawing substituted moieties, are well-tolerated, leading to target products in moderate to good yields.
Authors
- Jin‐Heng Li (ORCID: https://orcid.org/0000-0001-7215-7152)
- Yilin Liu (ORCID: https://orcid.org/0000-0002-8491-914X)
- Yang Li (ORCID: https://orcid.org/0000-0001-6026-4794)
- Qi Xue (ORCID: https://orcid.org/0000-0002-4043-7413)
- Shuaikang Ren
- Jiangfei Chen (ORCID: https://orcid.org/0009-0003-3279-2030)
Institutions
- Huaihua University (CN)
- Qingdao University of Science and Technology (CN)
- Lishui University (CN)
- Institute of Organic Synthesis (RU)
- Laboratoire de Synthèse Organique (FR)
- State Key Laboratory of Chemical Engineering (CN)
- State Key Laboratory of Applied Organic Chemistry
- Lanzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-21
- DOI
- https://doi.org/10.1021/acs.joc.5c00271
- Citations
- 1
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangxi Province
- Natural Science Foundation of Hunan Province
- Taishan Scholar Project of Shandong Province