Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates

Sydonie D. Schimler, Megan A. Cismesia, Patrick S. Hanley, Robert D.J. Froese, Matthew J. Jansma, Douglas C. Bland, Melanie S. Sanford

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)1452-1455
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number4
DOIs
StatePublished - Feb 1 2017

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    Schimler, S. D., Cismesia, M. A., Hanley, P. S., Froese, R. D. J., Jansma, M. J., Bland, D. C., & Sanford, M. S. (2017). Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates. Journal of the American Chemical Society, 139(4), 1452-1455. https://doi.org/10.1021/jacs.6b12911