3-(perfluorophenyl)quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(perfluorophenyl)quinoline
• 英文别名: 3-(2,3,4,5,6-Pentafluorophenyl)quinoline
• 化学式: C₁₅H₆F₅N
• 分子量: 295.211
• InChiKey: JEIGXVIBOXUUOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴喹啉 、 五氟苯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 potassium carbonate 作用下， 以 醋酸异丙酯 为溶剂， 反应 12.0h， 以92%的产率得到3-(perfluorophenyl)quinoline
  参考文献：
  名称：

  Mild and General Conditions for the Cross-Coupling of Aryl Halides with Pentafluorobenzene and Other Perfluoroaromatics

  摘要：

  New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.

  DOI：

  10.1021/ol0619967

文献信息

• C–O/C–H Coupling of Polyfluoroarenes with Aryl Carbamates by Cooperative Ni/Cu Catalysis
  作者：Yang Wang、Song-Bai Wu、Wen-Juan Shi、Zhang-Jie Shi

  DOI：10.1021/acs.orglett.6b00819

  日期：2016.6.3

  C–O and C–H bonds is reported. The reaction conditions are simple, and only transition-metal catalysts and ligands are essential. Mechanistic studies indicated that Ni catalyst played an important role in activating C–O bond, while the Cu one in activating C–H Bond. The developed system proved to be effective for cross-coupling of terminal alkynes with aryl carbamates.

  据报道，多氟芳烃与氨基甲酸芳基酯通过sp 2 C-O和CH-H键的裂解而发生交叉偶联。反应条件简单，仅过渡金属催化剂和配体是必需的。机理研究表明，镍催化剂在活化C-O键中起重要作用，而铜在活化C-H键中起重要作用。事实证明，开发的系统对于末端炔烃与氨基甲酸芳基酯的交叉偶联是有效的。
• Mild and General Conditions for the Cross-Coupling of Aryl Halides with Pentafluorobenzene and Other Perfluoroaromatics
  作者：Marc Lafrance、Daniel Shore、Keith Fagnou

  DOI：10.1021/ol0619967

  日期：2006.10.1

  New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.