Cu-Catalyzed Electrochemical Activation of Nitromethane to Access Aldoxime-Substituted Nitrile Oxide for Huisgen Reaction
Here, we report an electrochemical approach to generate an aldoxime-substituted nitrile oxide via the activation of nitromethane. The Cu-catalyzed Huisgen reaction of this 1,3-dipole with alkynes enables successful preparation of 48 new isoxazole aldoximes, which are typically challenging to synthesize by other methods, in 52 to 97% yields with excellent regioselectivity and chemoselectivity in a single step. Moreover, 20 3,3'-bisisoxazoles are prepared from the isoxazole aldoxime products in good yields via a two-step sequence.
Authors
- Yuexia Zhang (ORCID: https://orcid.org/0000-0002-2489-1253)
- Zhichao Shao (ORCID: https://orcid.org/0000-0003-3168-1016)
- Liumin Wang (ORCID: https://orcid.org/0000-0001-8004-5206)
- Lixing Zhao (ORCID: https://orcid.org/0000-0002-8185-1733)
- Meng Xue
- Shuying Liu (ORCID: https://orcid.org/0000-0002-5573-7574)
- Tao Pan (ORCID: https://orcid.org/0000-0001-9333-1412)
- Yulin Li (ORCID: https://orcid.org/0009-0003-2053-1458)
Institutions
- Qingdao University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-10
- DOI
- https://doi.org/10.1021/acs.orglett.4c04146
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Qingdao University
- Natural Science Foundation of Qingdao