Copper-Catalyzed Formal [4 + 1] Annulation of Diynes with Isoxazoles: Synthesis of Pyrrolo[3,4-<i>b</i>]indoles
Catalytic annulation of isoxazoles with alkynes is an efficient methodology for the assembly of N-heterocyclic architectures, and most reactions require noble-metal catalysts. Herein, we disclose a copper-catalyzed formal [4 + 1] annulation of 1,6-diynes with isoxazoles for the efficient and atom-economical construction of biologically important pyrrolo[3,4-<i>b</i>]indoles in high yields via vinyl cation intermediates, which is significantly different from previous annulations of alkynes with isoxazoles involving α-imino metal carbene intermediates. Interestingly, preliminary results have been obtained for the related catalytic atroposelective transformation. Computational mechanistic studies are employed to elucidate the reaction mechanism.
Authors
- Long‐Wu Ye (ORCID: https://orcid.org/0000-0003-3108-2611)
- Yijie Zheng (ORCID: https://orcid.org/0000-0002-6513-1584)
- Ya-Nan Meng
- Zhou Xu (ORCID: https://orcid.org/0000-0002-9703-8245)
- Li‐Gao Liu (ORCID: https://orcid.org/0000-0001-5002-7429)
- Bo Zhou (ORCID: https://orcid.org/0000-0002-5551-678X)
- Tian-Qi Hu
Institutions
- Xuzhou Medical College (CN)
- Xiamen University (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
- State Key Laboratory of Chemical Engineering (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c01406
- Citations
- 4
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Natural Science Foundation of Xiamen City
- National Natural Science Foundation of China
- Natural Science Foundation of Fujian Province
- Natural Science Foundation of Jiangsu Province
- Xuzhou Science and Technology Bureau
- Fundamental Research Funds for the Central Universities