title: Silver-catalyzed radical aminofluorination of unactivated alkenes in aqueous media.
abstract: We report herein a mild and catalytic intramolecular aminofluorination of unactivated alkenes. Thus, with the catalysis of AgNO3, the reactions of various N-arylpent-4-enamides with Selectfluor reagent in CH2Cl2/H2O led to the efficient synthesis of 5-fluoromethyl-substituted γ-lactams. A mechanism involving silver-catalyzed oxidative generation of amidyl radicals and silver-assisted fluorine atom transfer was proposed.
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, PR China.
authors.forename: Zhaodong
authors.initials: Z
authors.lastname: Li
authors.forename: Liyan
authors.initials: L
authors.lastname: Song
authors.forename: Chaozhong
authors.initials: C
authors.lastname: Li
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003979:Diazonium Compounds / Q000138:chemical synthesis / Q000737:chemistry; D054879:Halogenation; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012834:Silver / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D000475:Alkenes; D000588:Amines; D003979:Diazonium Compounds; D007769:Lactams; D014867:Water; D012834:Silver; C408750:selectfluor