title: Synthesis of 2-aryl-3-trifluoromethylquinolines using (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane.
abstract: The Hiyama cross-coupling reaction of (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane (1) with 2-iodoaniline (2) proceeded without any protection of the amino group. The coordination of copper(II) fluoride to 2,2'-bipyridyl provided the fluoride source required to trigger this reaction, affording (E)-2-(3,3,3-trifluoroprop-1-enyl)aniline (3). In the presence of a stoichiometric amount of [Cu(OTf)]2·C6H6, the treatment of 3 with an aryl aldehyde at 200 °C provided the 2-aryl-3-trifluoromethylquinoline (4) via the oxidative cyclization of an in situ-generated imine substructure.
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata 573-0101, Japan.
authors.forename: Masaaki
authors.initials: M
authors.lastname: Omote
authors.forename: Miyuu
authors.initials: M
authors.lastname: Tanaka
authors.forename: Miki
authors.initials: M
authors.lastname: Tanaka
authors.forename: Akari
authors.initials: A
authors.lastname: Ikeda
authors.forename: Atsushi
authors.initials: A
authors.lastname: Tarui
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Sato
authors.forename: Akira
authors.initials: A
authors.lastname: Ando
mesh_terms: D015082:2,2'-Dipyridyl / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D005459:Fluorides / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C552400:2-iodobenzenamine; D000447:Aldehydes; D000814:Aniline Compounds; D011804:Quinolines; D012821:Silanes; D015082:2,2'-Dipyridyl; C057829:copper fluoride; D003300:Copper; D005459:Fluorides