Intramolecular Friedel–Crafts Arylation of Achmatowicz Rearrangement Products for Construction of 1,5-Oxygen-Bridged Medium-Sized Carbocycles
The first intramolecular Friedel-Crafts arylation of Achmatowicz rearrangement (AchR) products is achieved, providing 1,5-oxygen-bridged medium-sized carbocycles 9-oxabicyclo[3.3.1]nonanes (9-OBNs) or 10-oxabicyclo[4.3.1]decanes (10-OBDs). The efficiency and utility of this protocol were demonstrated by a broad substrate scope (31 examples), excellent scalability (gram scale), and versatile transformations of products. Additionally, this FeCl<sub>3</sub> protocol allows for Prins cyclization of Achmatowicz rearrangement products and an intermolecular Friedel-Crafts reaction, which extends the application of Achmatowicz rearrangement.
Authors
- Lixin Liang (ORCID: https://orcid.org/0000-0003-1790-8472)
- Rongbiao Tong (ORCID: https://orcid.org/0000-0002-2740-5222)
- Shiji Chen (ORCID: https://orcid.org/0000-0002-5775-2516)
- Ming Wai Liaw (ORCID: https://orcid.org/0000-0002-0945-7969)
- Qingyun Huang (ORCID: https://orcid.org/0000-0001-8738-4382)
Institutions
- Guangxi University (CN)
- Hong Kong University of Science and Technology (HK)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-20
- DOI
- https://doi.org/10.1021/acs.orglett.5c02533
- Citations
- 3
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- Natural Science Foundation of Guangxi Zhuang Autonomous Region
- Research Grants Council, University Grants Committee
- Guangxi University