title: Silver-catalyzed radical phosphonofluorination of unactivated alkenes.
abstract: We report herein a mild and catalytic phosphonofluorination of unactivated alkenes. With catalysis by AgNO3, the condensation of various unactivated alkenes with diethyl phosphite and Selectfluor reagent in CH2Cl2/H2O/HOAc at 40 °C led to the efficient synthesis of β-fluorinated alkylphosphonates with good stereoselectivity and wide functional group compatibility. A mechanism involving silver-catalyzed oxidative generation of phosphonyl radicals and silver-assisted fluorine atom transfer is proposed.
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, P.R. China.
authors.forename: Chengwei
authors.initials: C
authors.lastname: Zhang
authors.forename: Zhaodong
authors.initials: Z
authors.lastname: Li
authors.forename: Lin
authors.initials: L
authors.lastname: Zhu
authors.forename: Limei
authors.initials: L
authors.lastname: Yu
authors.forename: Zhentao
authors.initials: Z
authors.lastname: Wang
authors.forename: Chaozhong
authors.initials: C
authors.lastname: Li
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012835:Silver Nitrate / Q000737:chemistry*
chemical_list: D000475:Alkenes; D003979:Diazonium Compounds; D006845:Hydrocarbons, Fluorinated; D009943:Organophosphorus Compounds; C408750:selectfluor; D012835:Silver Nitrate