title: Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion.
abstract: The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [(18)F]KF. This late-stage strategy provides an attractive route to (18)F-labeled biomolecules.
authors: Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
authors: Erin E
authors: EE
authors: Gray
authors: Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
authors: Matthew K
authors: MK
authors: Nielsen
authors: Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
authors: Kimberly A
authors: KA
authors: Choquette
authors: Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
authors: Julia A
authors: JA
authors: Kalow
authors: Translational Biomarkers, Merck Research Laboratories , West Point, Pennsylvania 19486, United States.
authors: Thomas J A
authors: TJ
authors: Graham
authors: Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
authors: Abigail G
authors: AG
authors: Doyle
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D054879:Halogenation; D006859:Hydrogen / Q000737:chemistry*; D017680:Potassium Compounds / Q000737:chemistry; D020005:Propanols / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated
chemical_list: D001391:Azo Compounds; D003300:Copper; D005459:Fluorides; D005461:Fluorine; D006859:Hydrogen; D017680:Potassium Compounds; D020005:Propanols; C001337:hexafluoroisopropanol; D006845:Hydrocarbons, Fluorinated; C033320:potassium fluoride