2,2'-{5,5'-bis(trifluoromethyl)-1,1'-biphenyl-2,2'-diyl}bispyridine | 1151554-19-6

• 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'-{5,5'-bis(trifluoromethyl)-1,1'-biphenyl-2,2'-diyl}bispyridine
• 英文别名: 2,2'-(5,5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2,2'-diyl)dipyridine；2,2'-(5,5'-bis(trifluoromethyl)biphenyl-2,2'-diyl)-dipyridine；2-[2-[2-Pyridin-2-yl-5-(trifluoromethyl)phenyl]-4-(trifluoromethyl)phenyl]pyridine；2-[2-[2-pyridin-2-yl-5-(trifluoromethyl)phenyl]-4-(trifluoromethyl)phenyl]pyridine
• CAS: 1151554-19-6
• 化学式: C₂₄H₁₄F₆N₂
• 分子量: 444.379
• InChiKey: FQHRSURCZUXTCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-[4-(三氟甲基)苯基]吡啶 在 硫酸 、 碘 、 palladium diacetate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以65%的产率得到2,2'-{5,5'-bis(trifluoromethyl)-1,1'-biphenyl-2,2'-diyl}bispyridine
  参考文献：
  名称：

  钯催化芳烃使用阳极氧化的区域选择性均偶联：芳烃碳氢键的形式电解

  摘要：

  在存在I 2的情况下，在阳极氧化条件下实现了芳基吡啶的钯催化区域选择性均偶联。间取代的芳基吡啶的二聚化在较少空间拥挤的邻位上选择性地进行，并且选择性与报道的使用氧酮作为氧化剂的钯催化的二聚化的选择性不同。在电化学反应条件下，还使用催化量的Pd（OAc）2和I 2进行二聚。

  DOI：

  10.1021/om500957a

文献信息

• Palladium-Catalyzed Regioselective Homocoupling of Arenes Using Anodic Oxidation: Formal Electrolysis of Aromatic Carbon–Hydrogen Bonds
  作者：Fumito Saito、Hiroko Aiso、Takuya Kochi、Fumitoshi Kakiuchi

  DOI：10.1021/om500957a

  日期：2014.11.24

  arylpyridines proceeded selectively at less-sterically congested ortho-positions, and the selectivity is different from that reported for the palladium-catalyzed dimerization using Oxone as an oxidant. The dimerization also proceeds using catalytic amounts of both Pd(OAc)2 and I2 under the electrochemical reaction conditions.

  在存在I 2的情况下，在阳极氧化条件下实现了芳基吡啶的钯催化区域选择性均偶联。间取代的芳基吡啶的二聚化在较少空间拥挤的邻位上选择性地进行，并且选择性与报道的使用氧酮作为氧化剂的钯催化的二聚化的选择性不同。在电化学反应条件下，还使用催化量的Pd（OAc）2和I 2进行二聚。
• Cu(II)-mediated oxidative dimerization of 2-phenylpyridine derivatives
  作者：Xiao Chen、Graham Dobereiner、Xue-Shi Hao、Ramesh Giri、Nathan Maugel、Jin-Quan Yu

  DOI：10.1016/j.tet.2008.10.053

  日期：2009.4

  A Cu(II)/I-2-mecliated C-H bond activation is described. A variety of 2-phenylpyridine derivatives are oxidatively dimerized at the ortho-position of the phenyl ring in which a net loss of two hydrogen atoms results ill [lie formation of a biaryl compound via a double C-H activation/C-C bond-forming process. Moderate functional group tolerance was observed on both the aryl and the pyridyl rings. A single electron transfer (SET) or electrophilic metalation process for iodination followed by Ullmann Coupling Of the intermediate iodinated product is proposed as the operating mechanism for the dimerization process. (C) 2008 Published by Ekevier Ltd.
• 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.