Bifunctional Lewis Base-Catalyzed (3 + 2) Cycloadditions of Pyrazolone-Derived MBH Carbonates with Arynes
The (3 + 2) cycloaddition of arynes with allylic ylides remains a formidable challenge because both intermediates are highly reactive and prone to spontaneous quenching. Here, we report a (3 + 2) cycloaddition of pyrazolone MBH carbonates with arynes, enabling the efficient synthesis of diverse indene-fused spiropyrazolones. The key is employing a new bifunctional Lewis base catalyst to facilitate the cycloaddition of <i>in situ</i> generated allylic pyridinium ylides with arynes.
Authors
- Cheng Peng
- Gu Zhan (ORCID: https://orcid.org/0000-0002-5263-8263)
- Bo Han (ORCID: https://orcid.org/0000-0003-3200-4682)
- Yuling Wu (ORCID: https://orcid.org/0000-0002-2686-2835)
- Yiqiao Gu
- Laiping Yao
Institutions
- Chengdu University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-16
- DOI
- https://doi.org/10.1021/acs.orglett.4c03410
- Citations
- 4
- Primary Topic
- Cyclization and Aryne Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- State Administration of Traditional Chinese Medicine of the People's Republic of China
- Sichuan Province Science and Technology Support Program