Nucleophilic Deoxyfluorination of Phenols via Aryl Fluorosulfonate Intermediates
| Autor: | Patrick S. Hanley, Douglas C. Bland, Robert D. J. Froese, Megan A. Cismesia, Matthew J. Jansma, Melanie S. Sanford, Sydonie D. Schimler |
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| Rok vydání: | 2017 |
| Předmět: |
Fluorosulfonate
010405 organic chemistry Aryl General Chemistry Bond formation 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry chemistry Nucleophile Ab initio quantum chemistry methods Tetramethylammonium fluoride Organic chemistry Phenols Sulfuryl fluoride |
| Zdroj: | Journal of the American Chemical Society. 139:1452-1455 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.6b12911 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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