Divergent Access to Polycyclic Fluorenofuran Systems via Palladium-Catalyzed Cascade Furan-Participated Diels–Alder Cycloaddition Reactions
The Pd-catalyzed reaction of 1-(2-iodophenyl)-3-arylprop-2-yn-1-ones with benzene-tethered furan-ynes produces novel fused hexacyclic indenone-furan scaffolds, while the reaction with propargyl furfuryl ethers affords the pentacyclic indenone-spirodifuran system. The thiophene-containing alkynes also proceed by similar transformations. A mechanism involving the Pd-catalyzed coupling and propargylic Alder-ene reaction to generate the indenone-allene intermediate, followed by an intramolecular furan/thiophene-participated inverse electron-demand Diels-Alder reaction, is proposed.
Authors
- Ting Xia
- Ruwei Shen (ORCID: https://orcid.org/0000-0002-8834-3256)
- Shugao Zhu (ORCID: https://orcid.org/0000-0001-8814-4161)
- Yu Lan (ORCID: https://orcid.org/0000-0002-2328-0020)
- Shihan Liu (ORCID: https://orcid.org/0000-0002-5886-0260)
- Rui Zhang (ORCID: https://orcid.org/0000-0001-5674-7283)
- Rongjing Yu
Institutions
- Nanjing Tech University (CN)
- Nanchang University (CN)
- Chongqing University (CN)
- Henan University (CN)
- Zhengzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-06
- DOI
- https://doi.org/10.1021/acs.orglett.4c03692
- Citations
- 6
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- National Natural Science Foundation of China
- Nanchang University