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Updated: May 30, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Intramolecular Fluoroacylation Enabled by TrBF4-Catalyzed Fluoride Recycling
Ali McKnight1, Yuriko H Fujisato1, Namrata Khanal2
1Department of Chemistry, York University, Toronto, Ontario M3J 1P3, Canada.
Abstract:
Alkyne- and alkene-tethered acyl fluorides undergo intramolecular carbofluorination via fluoride recycling using catalytic TrBF4. Excellent stereoselectivity is observed for the alkyne addition, enabling access to novel fluorinated indan-2-ones (all ≥95:5 E/Z) and cyclopentan-2-ones (85:15 E/Z). 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.
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