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Updated: Jun 4, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
FON: An Innovative Fluorinated Group via Hydroetherification-Type Reactivity
Sanaz Rajabalinia1, Hedieh Lotfian1, Sabrina Hoford1
1Department of Chemistry, Brock University, St. Catharines, Ontario L2S 3A1, Canada.
Abstract:
An efficient strategy for preparing the novel O-difluoroalkylhydroxylamine fluorinated functional group, coined FON, is reported. This analogue of medicinally important β-phenethyl ether scaffolds in uniting gem-difluoro and N-O moieties is synthesized in one step via chemo- and regioselectivity metal-free hydroetherification-type additions. As shown, this unique mode of reactivity is realized for a diverse substrate scope and applied to gram-scale synthesis and site-selective deuterium incorporation. Lastly, a mechanistic understanding with implications in Brønsted acid catalysis is offered.
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