title: One-pot, two-step, microwave-assisted palladium-catalyzed conversion of aryl alcohols to aryl fluorides via aryl nonaflates.
abstract: A convenient procedure for converting aryl alcohols to aryl fluorides via aryl nonafluorobutylsulfonates (ArONf) is presented. Moderate to good one-pot, two-step yields were achieved by this nonaflation and microwave-assisted, palladium-catalyzed fluorination sequence. The reductive elimination step was investigated by DFT calculations to compare fluorination with chlorination, proving a larger thermodynamic driving force for the aryl fluoride product. Finally, a key aryl fluoride intermediate for the synthesis of a potent HCV NS3 protease inhibitor was smoothly prepared with the novel protocol.
authors.affiliation: KDev Exploratory AB, Nobels väg 3, SE-171 65 Solna, Sweden.
authors.forename: Johan
authors.initials: J
authors.lastname: Wannberg
authors.forename: Charlotta
authors.initials: C
authors.lastname: Wallinder
authors.forename: Meltem
authors.initials: M
authors.lastname: Ünlüsoy
authors.forename: Christian
authors.initials: C
authors.lastname: Sköld
authors.forename: Mats
authors.initials: M
authors.lastname: Larhed
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D005459:Fluorides / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D000438:Alcohols; D006845:Hydrocarbons, Fluorinated; D010165:Palladium; D005459:Fluorides