title: (18)F-Labeling of Aryl-SCF3, -OCF3 and -OCHF2 with [(18)F]Fluoride.
abstract: We report that halogenophilic silver(I) triflate permits halogen exchange (halex) nucleophilic (18)F-fluorination of aryl-OCHFCl, -OCF2Br and -SCF2Br precursors under mild conditions. This Ag(I)-mediated process allows for the first time access to a range of (18)F-labeled aryl-OCHF2, -OCF3 and -SCF3 derivatives, inclusive of [(18)F]riluzole. The (18)F-labeling of these medicinally important motifs expands the radiochemical space available for PET applications.
authors.affiliation: University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK).
authors.forename: Tanatorn
authors.initials: T
authors.lastname: Khotavivattana
authors.affiliation: University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK).
authors.forename: Stefan
authors.initials: S
authors.lastname: Verhoog
authors.affiliation: University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK).
authors.forename: Matthew
authors.initials: M
authors.lastname: Tredwell
authors.affiliation: University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK).
authors.forename: Lukas
authors.initials: L
authors.lastname: Pfeifer
authors.affiliation: University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK).
authors.forename: Samuel
authors.initials: S
authors.lastname: Calderwood
authors.affiliation: Medicines Discovery & Development, GlaxoSmithKline R&D, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY (UK).
authors.forename: Katherine
authors.initials: K
authors.lastname: Wheelhouse
authors.affiliation: Advion BioSystems, 10 Brown Road, Suite 101, Ithaca, NY 14850 (USA).
authors.forename: Thomas
authors.initials: T
authors.lastname: Lee Collier
authors.affiliation: University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK). veronique.gouverneur@chem.ox.ac.uk.
authors.forename: Véronique
authors.initials: V
authors.lastname: Gouverneur
mesh_terms: D005462:Fluorine Radioisotopes; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012834:Silver / Q000737:chemistry
chemical_list: D005462:Fluorine Radioisotopes; D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; D012834:Silver
keywords: [18F]fluoride; difluoromethyl ethers; halogen exchange; silver triflate; trifluoromethyl ethers