1,8-Di(2-ethynylaryl)biphenylenes: Palladium-Catalyzed Intramolecular Cycloisomerization and Subsequent Thermal Rearrangement
A cascade reaction for 1,8-dibromobiphenylene A with arylboronic acid B toward an unusual product C was comprehensively investigated. The initially formed Suzuki product D underwent an unprecedented palladium-catalyzed cycloisomerization, yielding E with a unique 5-8-5-membered ring framework. In most cases, E proceeded via thermal rearrangement to form C. This work also examined the scope and limitations of the cascade reaction, probed its mechanism, and verified the structures of C and E by X-ray crystallography.
Authors
- Yao‐Ting Wu (ORCID: https://orcid.org/0000-0001-7716-1855)
- Chien‐Hung Liu (ORCID: https://orcid.org/0000-0001-8918-5627)
- Mu‐Jeng Cheng (ORCID: https://orcid.org/0000-0002-8121-0485)
- Hsiang‐Han Chen (ORCID: https://orcid.org/0000-0003-1329-3298)
- Kuan-Hsun Huang (ORCID: https://orcid.org/0000-0001-8304-7151)
- Chia-Jung Yang (ORCID: https://orcid.org/0000-0002-0609-9262)
- Wei‐Ting Ou
Institutions
- National Cheng Kung University (TW)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-11
- DOI
- https://doi.org/10.1021/acs.orglett.5c04302
- Citations
- 1
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94