Intramolecular Fluoroacylation Enabled by TrBF<sub>4</sub>-Catalyzed Fluoride Recycling
Alkyne- and alkene-tethered acyl fluorides undergo intramolecular carbofluorination via fluoride recycling using catalytic TrBF<sub>4</sub>. Excellent stereoselectivity is observed for the alkyne addition, enabling access to novel fluorinated indan-2-ones (all ≥95:5 <i>E</i>/<i>Z</i>) and cyclopentan-2-ones (85:15 <i>E</i>/<i>Z</i>). Fluorinated chroman-2-ones and tertiary alkyl fluorides can also be synthesized using this method, comparing favorably to previously reported protocols that employ expensive metal catalysts under harsher conditions.
Authors
- Christine M. Le (ORCID: https://orcid.org/0000-0003-2543-4414)
- Namrata Khanal
- Yuriko H. Fujisato
- Alice A. Mcknight
Institutions
- University of New Mexico (US)
- York University (CA)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-01-27
- DOI
- https://doi.org/10.1021/acs.orglett.5c00154
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- American Chemical Society Petroleum Research Fund
- Natural Sciences and Engineering Research Council of Canada