Synthesis of 2-Aryl-3-trifluoromethylquinolines Using (E)-Trimethyl(3,3,3-trifluoroprop-1-enyl)silane

被引：16

作者：

Omote, Masaaki ^{[1
]}

Tanaka, Miyuu ^{[1
]}

Tanaka, Miki ^{[1
]}

Ikeda, Akari ^{[1
]}

Tarui, Atsushi ^{[1
]}

Sato, Kazuyuki ^{[1
]}

Ando, Akira ^{[1
]}

机构：

[1] Setsunan Univ, Fac Pharmaceut Sci, Hirakata, Osaka 5730101, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 12期

关键词：

REGIOSELECTIVE SYNTHESIS; SUBSTITUTED QUINOLINES; CONVENIENT SYNTHESIS; BORONIC ACIDS; TRIFLUOROMETHYLATION; ARYL; RESISTANCE; CHLORIDES; ANILINES;

D O I：

10.1021/jo400859s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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)center dot C6H6, the treatment of 3 with an aryl aldehyde at 200 degrees C provided the 2-aryl-3-trifluoromethylquinoline (4) via the oxidative cyclization of an in situ-generated imine substructure.

引用

页码：6196 / 6201

页数：6

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