Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata 573-0101, Japan.
J Org Chem. 2013 Jun 21;78(12):6196-201. doi: 10.1021/jo400859s. Epub 2013 Jun 4.
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.
(E)-三甲基(3,3,3-三氟丙-1-烯基)硅烷(1)与2-碘苯胺(2)的 Hiyama 交叉偶联反应在氨基未保护的情况下进行。铜(II)氟化物与 2,2'-联吡啶的配位提供了触发此反应所需的氟源，得到(E)-2-(3,3,3-三氟丙-1-烯基)苯胺(3)。在[Cu(OTf)]2·C6H6 的化学计量存在下，在 200°C 下用芳基醛处理 3 可通过原位生成的亚胺结构的氧化环化提供 2-芳基-3-三氟甲基喹啉(4)。
