Nucleophilic Deoxyfluorination of Phenols via Aryl Fluorosulfonate Intermediates
2017
Schimler, Sydonie D. | Cismesia, Megan A. | Hanley, Patrick S. | Froese, Robert D. J. | Jansma, Matthew J. | Bland, Douglas C. | Sanford, Melanie S.
This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO₂F₂) and tetramethylammonium fluoride (NMe₄F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe₄F proceeds under mild conditions (often at room temperature) to afford a broad range of electronically diverse and functional group-rich aryl fluoride products. This transformation was then translated to a one-pot conversion of phenols to aryl fluorides using the combination of SO₂F₂ and NMe₄F. Ab initio calculations suggest that carbon–fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.
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