title: Metal-free intramolecular aminofluorination of alkenes mediated by PhI(OPiv)2/hydrogen fluoride-pyridine system.
abstract: A convenient, metal-free intramolecular aminofluorination of alkenes has been developed. Employing readily available PhI(OPiv)(2) and hydrogen fluoride-pyridine in the presence of BF(3)·OEt(2), tosyl-protected pent-4-en-1-amines were converted to 3-F-piperidines in one step in good yields as well as high stereoselectivity.
authors.affiliation: The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, PR China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Wang
authors.forename: Wenhe
authors.initials: W
authors.lastname: Zhong
authors.forename: Xiong
authors.initials: X
authors.lastname: Wei
authors.forename: Maoheng
authors.initials: M
authors.lastname: Ning
authors.forename: Xiangbao
authors.initials: X
authors.lastname: Meng
authors.forename: Zhongjun
authors.initials: Z
authors.lastname: Li
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D006858:Hydrofluoric Acid / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C579463:3-fluorine-piperidine; D000475:Alkenes; D010880:Piperidines; D011725:Pyridines; D014753:Vinyl Compounds; D007455:Iodine; C023666:pyridine; D006858:Hydrofluoric Acid