title: Selective anti-Markovnikov cyclization and hydrofluorination reaction in superacid HF/SbF5: a tool in the design of nitrogen-containing (fluorinated) polycyclic systems.
abstract: The selective synthesis of tetrahydroquinolines and fluorinated arylamines was performed in superacid HF/SbF5 through a superelectrophilic ammonium-carbenium activation process. This anti-Markovnikov oriented reaction was applied to the straightforward synthesis of highly valued (fluorinated) nitrogen-containing heterocyclic compounds.
authors.affiliation: Superacid group in Organic Synthesis team, Université de Poitiers, CNRS UMR 7285 IC2MP, 4, avenue Michel Brunet, F-86022 Poitiers Cedex, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Compain
authors.forename: Céline
authors.initials: C
authors.lastname: Bonneau
authors.forename: Agnès
authors.initials: A
authors.lastname: Martin-Mingot
authors.forename: Sébastien
authors.initials: S
authors.lastname: Thibaudeau
mesh_terms: D000965:Antimony / Q000737:chemistry*; D003500:Cyclization; D015195:Drug Design; D005459:Fluorides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006858:Hydrofluoric Acid / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006845:Hydrocarbons, Fluorinated; D011083:Polycyclic Compounds; D011804:Quinolines; C529140:antimony pentafluoride; D000965:Antimony; C542964:1,2,3,4-tetrahydroquinoline; D005459:Fluorides; D006858:Hydrofluoric Acid