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 in | Journal of the American Chemical Society Vol. 139; no. 4; pp. 1452 - 1455 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.02.2017
Amer Chemical Soc |
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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. |
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| AbstractList | 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. This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO F ) and tetramethylammonium fluoride (NMe F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe F 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 SO F and NMe F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate. |
| Author | Schimler, Sydonie D Cismesia, Megan A Froese, Robert D. J Hanley, Patrick S Jansma, Matthew J Sanford, Melanie S Bland, Douglas C |
| AuthorAffiliation | Department of Chemistry University of Michigan Core Research & Development The Dow Chemical Company |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: The Dow Chemical Company – name: University of Michigan – name: Core Research & Development |
| Author_xml | – sequence: 1 givenname: Sydonie D surname: Schimler fullname: Schimler, Sydonie D – sequence: 2 givenname: Megan A surname: Cismesia fullname: Cismesia, Megan A – sequence: 3 givenname: Patrick S surname: Hanley fullname: Hanley, Patrick S – sequence: 4 givenname: Robert D. J surname: Froese fullname: Froese, Robert D. J – sequence: 5 givenname: Matthew J surname: Jansma fullname: Jansma, Matthew J – sequence: 6 givenname: Douglas C surname: Bland fullname: Bland, Douglas C – sequence: 7 givenname: Melanie S orcidid: 0000-0001-9342-9436 surname: Sanford fullname: Sanford, Melanie S email: mssanfor@umich.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28111944$$D View this record in MEDLINE/PubMed |
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| Snippet | This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO2F2) and tetramethylammonium fluoride (NMe4F) via aryl... This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO F ) and tetramethylammonium fluoride (NMe F) via aryl... |
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| Title | Nucleophilic Deoxyfluorination of Phenols via Aryl Fluorosulfonate Intermediates |
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