FON: An Innovative Fluorinated Group via Hydroetherification-Type Reactivity

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.