2,2'-Di-2-pyridyl-3,3'-bithiophen | 63283-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2,2'-Di-2-pyridyl-3,3'-bithiophen
• 英文别名: 2,2'-di(pyridin-2-yl)-3,3'-bithiophene；2,2'-Di-(2-pyridyl)-3,3-bithienyl；2,2'-[3,3']bithiophenyl-2,2'-diyl-bis-pyridine；2,2'-([3,3'-Bithiophene]-2,2'-diyl)dipyridine；2-[3-(2-pyridin-2-ylthiophen-3-yl)thiophen-2-yl]pyridine
• CAS: 63283-00-1
• 化学式: C₁₈H₁₂N₂S₂
• 分子量: 320.439
• InChiKey: MXENDDDJURCSKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 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：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-噻吩基)吡啶 在 palladium diacetate Oxone 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 17.0h， 以44%的产率得到2,2'-Di-2-pyridyl-3,3'-bithiophen
  参考文献：
  名称：

  Highly Regioselective Catalytic Oxidative Coupling Reactions:  Synthetic and Mechanistic Investigations

  摘要：

  A highly efficient and regioselective Pd-catalyzed method for the oxidative coupling of arylpyridine derivatives is reported. Remarkably, the reactions proceed at room temperature and are compatible with diverse functionalities, including aryl halides and thiophenes. Mechanistic studies suggest that these transformations proceed via a previously unprecedented mechanism involving two different pyridine-directed C-H activation reactions-one at a PdII center and one at PdIV.

  DOI：

  10.1021/ja065718e

文献信息

• Highly Regioselective Catalytic Oxidative Coupling Reactions:  Synthetic and Mechanistic Investigations
  作者：Kami L. Hull、Erica L. Lanni、Melanie S. Sanford

  DOI：10.1021/ja065718e

  日期：2006.11.1

  A highly efficient and regioselective Pd-catalyzed method for the oxidative coupling of arylpyridine derivatives is reported. Remarkably, the reactions proceed at room temperature and are compatible with diverse functionalities, including aryl halides and thiophenes. Mechanistic studies suggest that these transformations proceed via a previously unprecedented mechanism involving two different pyridine-directed C-H activation reactions-one at a PdII center and one at PdIV.
• Kauffmann, Thomas; Otter, Rolf; Greving, Bernd, Chemische Berichte, 1983, vol. 116, # 2, p. 479 - 491
  作者：Kauffmann, Thomas、Otter, Rolf、Greving, Bernd、Koenig, Johann、Mitschker, Alfred、et al.

  DOI：——

  日期：——
• 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.