title: A fluoride-derived electrophilic late-stage fluorination reagent for PET imaging.
abstract: The unnatural isotope fluorine-18 ((18)F) is used as a positron emitter in molecular imaging. Currently, many potentially useful (18)F-labeled probe molecules are inaccessible for imaging because no fluorination chemistry is available to make them. The 110-minute half-life of (18)F requires rapid syntheses for which [(18)F]fluoride is the preferred source of fluorine because of its practical access and suitable isotope enrichment. However, conventional [(18)F]fluoride chemistry has been limited to nucleophilic fluorination reactions. We report the development of a palladium-based electrophilic fluorination reagent derived from fluoride and its application to the synthesis of aromatic (18)F-labeled molecules via late-stage fluorination. Late-stage fluorination enables the synthesis of conventionally unavailable positron emission tomography (PET) tracers for anticipated applications in pharmaceutical development as well as preclinical and clinical PET imaging.
authors: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
authors: Eunsung
authors: E
authors: Lee
authors: Adam S
authors: AS
authors: Kamlet
authors: David C
authors: DC
authors: Powers
authors: Constanze N
authors: CN
authors: Neumann
authors: Gregory B
authors: GB
authors: Boursalian
authors: Takeru
authors: T
authors: Furuya
authors: Daniel C
authors: DC
authors: Choi
authors: Jacob M
authors: JM
authors: Hooker
authors: Tobias
authors: T
authors: Ritter
mesh_terms: D005459:Fluorides / Q000737:chemistry; D005462:Fluorine Radioisotopes / Q000737:chemistry; D054879:Halogenation; D007202:Indicators and Reagents; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D049268:Positron-Emission Tomography / Q000379:methods*
chemical_list: D005462:Fluorine Radioisotopes; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D010165:Palladium; D005459:Fluorides