title: Nucleophilic Deoxyfluorination of Phenols via Aryl Fluorosulfonate Intermediates.
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 SO2F2and NMe4F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
authors.forename: Sydonie D
authors.initials: SD
authors.lastname: Schimler
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
authors.forename: Megan A
authors.initials: MA
authors.lastname: Cismesia
authors.affiliation: Core Research & Development, The Dow Chemical Company , 1710 Building, Midland, Michigan 48674, United States.
authors.forename: Patrick S
authors.initials: PS
authors.lastname: Hanley
authors.affiliation: Core Research & Development, The Dow Chemical Company , 1710 Building, Midland, Michigan 48674, United States.
authors.forename: Robert D J
authors.initials: RD
authors.lastname: Froese
authors.affiliation: Core Research & Development, The Dow Chemical Company , 1710 Building, Midland, Michigan 48674, United States.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Jansma
authors.affiliation: Core Research & Development, The Dow Chemical Company , 1710 Building, Midland, Michigan 48674, United States.
authors.forename: Douglas C
authors.initials: DC
authors.lastname: Bland
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
authors.forename: Melanie S
authors.identifier: 0000-0001-9342-9436
authors.initials: MS
authors.lastname: Sanford