1-methyl-3-(pentafluorophenyl)-indole | 1244039-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-methyl-3-(pentafluorophenyl)-indole
• 英文别名: 1-methyl-3-(perfluorophenyl)-1H-indole；1-methyl-3-(2,3,4,5,6-pentafluorophenyl)indole
• CAS: 1244039-16-4
• 化学式: C₁₅H₈F₅N
• 分子量: 297.227
• InChiKey: WSQQJFXPJDGLAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(pentafluorophenyl)-indole 、 3,4-bis(4-chlorophenyl)-1H-pyrrole 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到1-Methyl-3-[2,3,4,5,6-pentakis[3,4-bis(4-chlorophenyl)pyrrol-1-yl]phenyl]indole
  参考文献：
  名称：

  Synthesis of a peripherally conjugated 5-6-7 nanographene

  摘要：

  通过5-6-7融合扩展杂芳族纳米石墨烯的结构，可以增强其近红外吸收和发射性能。

  DOI：

  10.1039/c5sc03280f
• 作为产物：
  描述：

  N-甲基咪唑 、 2,3,4,5,6-pentafluorophenyl(triphenylphosphine)gold(I) 在 碘苯二乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 22.0h， 以80%的产率得到1-methyl-3-(pentafluorophenyl)-indole
  参考文献：
  名称：

  Cross-coupling of arene–gold(III) complexes

  摘要：

  The reactivity of electron-deficient arene gold(III) complexes toward nucleophilic aromatic and heteraromatic counterparts has been studied. 1-Methylindole proved to be the best reaction partner while trimethoxybenzenes did not react. The ancillary ligand on gold also influenced the reactivity in the order PPh3>(PBu3)-Bu-t>IPr. An oxidative cross-coupling starting from the corresponding gold(I) complexes in presence of hypervalent iodide oxidants was also studied. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.029

文献信息

• Palladium-Catalyzed Aerobic Dehydrogenative Cross-Coupling of Polyfluoroarenes with Thiophenes: Facile Access to Polyfluoroarene–Thiophene Structure
  作者：Chun-Yang He、Qiao-Qiao Min、Xingang Zhang

  DOI：10.1021/om200873j

  日期：2012.2.27

  We report a Pd-catalyzed aerobic dehydrogenative cross-coupling of polyfluoroarenes with thiophenes via 2-fold C–H functionalization. The advantages of this reaction are its high reaction efficiency, excellent functional group compatibility, and use of molecular O2 as terminal oxidant. This reaction provides a useful and facile protocol for the preparation of polyfluoroarene–thiophene structure of

  我们通过2倍C–H功能化报告了Pd催化的多氟芳烃与噻吩的好氧脱氢交叉偶联。该反应的优点是反应效率高，官能团相容性好以及使用分子O 2作为末端氧化剂。该反应为制备功能材料中感兴趣的聚氟亚芳基-噻吩结构提供了一种有用且简便的方案。机理研究表明，该反应是由多氟芳烃的C–H键断裂引发的。
• Au-Catalyzed Cross-Coupling of Arenes via Double C–H Activation
  作者：Xacobe C. Cambeiro、Nanna Ahlsten、Igor Larrosa

  DOI：10.1021/jacs.5b10593

  日期：2015.12.23

  The first methodology for Au(I/III)-catalyzed oxidative cross-coupling of arenes via double C-H activation has been developed. The reaction is fully selective for the cross-coupling between electron-rich hetero-/carbocyclic arenes and electron-poor arenes bearing relatively acidic C-H bonds: The inherently high cross-selectivity of the system obviates the need for directing groups or a large excess of one of the coupling partners.
• Pd-Catalyzed Oxidative Cross-Coupling of Perfluoroarenes with Aromatic Heterocycles
  作者：Chun-Yang He、Shilu Fan、Xingang Zhang

  DOI：10.1021/ja106046p

  日期：2010.9.22

  A straightforward and practical method for direct Pd(OAc)(2)-catalyzed oxidative cross-coupling of electron-deficient perfluoroarenes with aromatic heterocycles has been developed. Because of its low catalyst loading (2.5 mol %), high reaction efficiency, good chemo- and regioselectivity, and excellent functional-group compatibility, this protocol provides a useful and operationally simple access to perfluoroarene thiophene structures of interest in functional materials for electronic devices.