Nucleophilic Deoxyfluorination of Phenols via Aryl Fluorosulfonate Intermediates

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 tempera...

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Published inJournal of the American Chemical Society Vol. 139; no. 4; pp. 1452 - 1455
Main Authors Schimler, Sydonie D, Cismesia, Megan A, Hanley, Patrick S, Froese, Robert D. J, Jansma, Matthew J, Bland, Douglas C, Sanford, Melanie S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.02.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
REPLACEMENT
ROOM-TEMPERATURE
FLUORINATION
PHARMACEUTICALS
FLUORIDE
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Summary: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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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b12911