2,2'-(3,3',5,5'-tetrafluoro-[1,1'-biphenyl]-2,2'-diyl)dipyridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2'-(3,3',5,5'-tetrafluoro-[1,1'-biphenyl]-2,2'-diyl)dipyridine
• 英文别名: 2-[2-(3,5-Difluoro-2-pyridin-2-ylphenyl)-4,6-difluorophenyl]pyridine；2-[2-(3,5-difluoro-2-pyridin-2-ylphenyl)-4,6-difluorophenyl]pyridine
• 化学式: C₂₂H₁₂F₄N₂
• 分子量: 380.344
• InChiKey: WSOHWCDRGIEAQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(2,4-二氟苯基)吡啶 在 iron(III) chloride 、 ruthenium-carbon composite 作用下， 以 甲苯 为溶剂， 以63 %的产率得到2,2'-(3,3',5,5'-tetrafluoro-[1,1'-biphenyl]-2,2'-diyl)dipyridine
  参考文献：
  名称：

  Cross‐Dehydrogenative Homocoupling of 2‐Aryl‐N‐heterocycles and Application to the Synthesis of Phenylpyridine Borane Dimers

  摘要：

  AbstractA method for the synthesis of 2‐aryl‐N‐heterocyclic dimers via a cross‐dehydrogenative homocoupling (homo‐CDC) has been developed using commercially available Ruthenium on charcoal as catalyst and iron trichloride as oxidant. A large variety of heterocyclic scaffolds and functional groups are tolerated and a complete regioselectivity resulting from the activation of the less sterically hindered C−H bonds was observed for meta‐substituted substrates. Starting from several homocoupling products obtained, a series of pyridine‐borane complexes was synthesized and the impact of the dimerization on their photophysical properties was studied and rationalized using theoretical calculations.

  DOI：

  10.1002/ejoc.202201164

文献信息

• Tetraalkylammonium-based ionic liquids for a RuCl3 catalyzed C–H activated homocoupling
  作者：Maren Muntzeck、Felix Pippert、René Wilhelm

  DOI：10.1016/j.tet.2020.131314

  日期：2020.7

  [BuEt3N][NTf2] can be a superior ionic liquid in a RuCl3 catalyzed oxidative C-H activation reaction compared to standard imidazolium-based ionic liquids. The tetraalkylammonium-based ionic liquid resulted in higher yields. This could be due to the absence of a possible C-H activation on the tetraalkylammonium-based ionic liquid itself. This side reaction could occur with imidazolium-based ionic liquids. The ionic liquid could be recycled and different oxidation agents could be used in the reaction. The best results were obtained with FeCl3 center dot 6H(2)O and with a combination of LiCl under an oxygen atmosphere. Up to 83% yield were obtained in the homocoupling of 2-arylpyridines. (C) 2020 Elsevier Ltd. All rights reserved.
• Cross‐Dehydrogenative Homocoupling of 2‐Aryl‐N‐heterocycles and Application to the Synthesis of Phenylpyridine Borane Dimers
  作者：Longhui Gao、Sophie Feuillastre、Gilles Clavier、Grégory Pieters

  DOI：10.1002/ejoc.202201164

  日期：——

  AbstractA method for the synthesis of 2‐aryl‐N‐heterocyclic dimers via a cross‐dehydrogenative homocoupling (homo‐CDC) has been developed using commercially available Ruthenium on charcoal as catalyst and iron trichloride as oxidant. A large variety of heterocyclic scaffolds and functional groups are tolerated and a complete regioselectivity resulting from the activation of the less sterically hindered C−H bonds was observed for meta‐substituted substrates. Starting from several homocoupling products obtained, a series of pyridine‐borane complexes was synthesized and the impact of the dimerization on their photophysical properties was studied and rationalized using theoretical calculations.