title: Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.
abstract: Hydrogen fluoride (HF) and selected nonbasic and weakly coordinating (toward cationic metal) hydrogen-bond acceptors (e.g., DMPU) can form stable complexes through hydrogen bonding. The DMPU/HF complex is a new nucleophilic fluorination reagent that has high acidity and is compatible with cationic metal catalysts. The gold-catalyzed mono- and dihydrofluorination of alkynes using the DMPU/HF complex yields synthetically important fluoroalkenes and gem-difluoromethlylene compounds regioselectively.
authors.affiliation: Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States.
authors.forename: Otome E
authors.initials: OE
authors.lastname: Okoromoba
authors.forename: Junbin
authors.initials: J
authors.lastname: Han
authors.forename: Gerald B
authors.initials: GB
authors.lastname: Hammond
authors.forename: Bo
authors.initials: B
authors.lastname: Xu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006858:Hydrofluoric Acid / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure
chemical_list: D000480:Alkynes; D006845:Hydrocarbons, Fluorinated; D006046:Gold; D006858:Hydrofluoric Acid