Synthesis of Epimino-Bridged Fullerene-Fused Tetrahydroazepines via 1,3-Dipolar Cycloaddition of [60]Fullerene with in Situ Generated Azomethine Ylides
A series of unique epimino-bridged fullerene-fused tetrahydroazepine derivatives were synthesized in moderate to good yields by the simple one-step reaction of [60]fullerene with primary amines in the presence of <i>N</i>-(3-bromopropyl)phthalimide with the addition of Pb<sub>2</sub>(OAc)<sub>2</sub>(OH)<sub>2</sub> and (CH<sub>3</sub>)<sub>3</sub>COK. The current protocol for the preparation of epimino-bridged fullerene bicyclic compounds via the 1,3-dipolar cycloaddition strategy has never been reported previously. A possible reaction mechanism is proposed to elucidate the generation of the obtained products based on control experiments and density functional theory (DFT) calculations.
Authors
- Wangqiang Shen (ORCID: https://orcid.org/0000-0002-8711-3934)
- Shi Bai (ORCID: https://orcid.org/0000-0003-2126-450X)
- Fa‐Bao Li (ORCID: https://orcid.org/0000-0002-1873-3128)
- Li Liu (ORCID: https://orcid.org/0000-0002-3684-4032)
- Ping Wu
- Zhengqing Yang (ORCID: https://orcid.org/0000-0002-6530-8693)
- Cheng Zhou (ORCID: https://orcid.org/0009-0006-7462-7211)
- Shunxin Zhao
Institutions
- Hefei University of Technology (CN)
- Dezhou University (CN)
- Hubei University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c01756
- Primary Topic
- Fullerene Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China