Yb(OTf)<sub>3</sub>‐Catalyzed C=C Bond Cleavage‐Reassembly Enabling Bicyclization: Regioselective Synthesis of Heteroarylated Pentacyclic Indoles
Abstract An Yb(OTf) 3 ‐catalyzed [2+2] cycloaddition /retro‐electrocyclization (CA‐RE)/bicyclization of 1‐(2‐aminoarylaklynyl)‐naphthalen‐2‐ols and 3‐alkylideneoxindoles is reported, enabling a direct C=C bond cleavage‐reassembly process to regioselectively synthesize a variety of quinoline‐tethered benzo[5,6]chromeno[2,3‐ b ]indoles in 31–84% yields. Exchanging the amino group for a hydroxyl group in the arylalkynyl unit of the naphthalen‐2‐ol substrate resulted in chromenyl chromeno[2,3‐ b ]indoles via a similar cascade process.
Authors
- Yinping Liu (ORCID: https://orcid.org/0000-0001-5468-2148)
- Qiuyun Li
- Chi‐Fan Zhu
- Ke Chen (ORCID: https://orcid.org/0000-0003-2384-8437)
- Bo Jiang (ORCID: https://orcid.org/0000-0003-3878-515X)
- Zili Liu (ORCID: https://orcid.org/0000-0002-6515-3433)
- Shuliang Wang (ORCID: https://orcid.org/0000-0002-7749-6628)
- Hao Wen (ORCID: https://orcid.org/0000-0002-8407-0369)
Institutions
- Jiangsu Normal University (CN)
- Changzhou University (CN)
- Yancheng Institute of Technology (CN)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-09-02
- DOI
- https://doi.org/10.1002/adsc.202400995
- Citations
- 2
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50