1-ethyl-2-(4-bromophenyl)imidazo[1,2-a]pyridinium iodide | 1463476-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-ethyl-2-(4-bromophenyl)imidazo[1,2-a]pyridinium iodide
• 英文别名: 2-(4-bromophenyl)-1-ethylimidazo[1,2-a]pyridinium iodide
• CAS: 1463476-27-8
• 化学式: C₁₅H₁₄BrN₂*I
• 分子量: 429.098
• InChiKey: ZBSMKHPQFFZKRE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  8.29
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  吡啶 、 1-ethyl-2-(4-bromophenyl)imidazo[1,2-a]pyridinium iodide 、 palladium dichloride 在 potassium carbonate 作用下， 反应 16.0h， 以44%的产率得到trans-{(1-ethyl-2-(4-bromophenyl)imidazol-3-ylidene[1,2-a]pyridine)}PdI₂(pyridine)
  参考文献：
  名称：

  Palladium complexes of the N-fused heterocycle derived abnormal N-heterocyclic carbenes for the much-preferred Cu-free and the amine-free Sonogashira coupling in air

  摘要：

  Abnormal N-heterocyclic carbenes of the N-fused heterocycles were employed in stabilizing a series of PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed complexes of the type (abnormal-NHC)Pdl(2)(pyridine). Specifically, imidazo[1,2-a]pyridine based abnormal complexes, trans-{(1-ethyl-2-(4-R-phenyl)-imidazol-3-ylidene[1,2-a]pyridine)}Pdl(2)(pyridine) [R= F (1b), Cl (2b), Br (3b) and Me (4b)] were synthesized from the reaction of corresponding imidazo[1,2-a]pyridinium iodide salts (1-4)a with PdCl2 in pyridine in the presence of K2CO3 as a base. The (1-4)b complexes carried out the Sonogashira couplings of the aryl bromide and iodide substrates with terminal alkynes in a mixed aqueous medium in air under the Cu-free and amine-free conditions. The density functional theory studies revealed that in the (1-4)b complexes, the C-carbene-Pd sigma-bonding interaction was significantly stronger than the trans Pd-N-pyridine sigma-bonding interaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.01.062
• 作为产物：
  描述：

  2-(4-溴苯基)咪唑并[1,2-a]吡啶 、 碘乙烷 以 乙腈 为溶剂， 反应 18.0h， 以62%的产率得到1-ethyl-2-(4-bromophenyl)imidazo[1,2-a]pyridinium iodide
  参考文献：
  名称：

  Palladium complexes of the N-fused heterocycle derived abnormal N-heterocyclic carbenes for the much-preferred Cu-free and the amine-free Sonogashira coupling in air

  摘要：

  Abnormal N-heterocyclic carbenes of the N-fused heterocycles were employed in stabilizing a series of PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed complexes of the type (abnormal-NHC)Pdl(2)(pyridine). Specifically, imidazo[1,2-a]pyridine based abnormal complexes, trans-{(1-ethyl-2-(4-R-phenyl)-imidazol-3-ylidene[1,2-a]pyridine)}Pdl(2)(pyridine) [R= F (1b), Cl (2b), Br (3b) and Me (4b)] were synthesized from the reaction of corresponding imidazo[1,2-a]pyridinium iodide salts (1-4)a with PdCl2 in pyridine in the presence of K2CO3 as a base. The (1-4)b complexes carried out the Sonogashira couplings of the aryl bromide and iodide substrates with terminal alkynes in a mixed aqueous medium in air under the Cu-free and amine-free conditions. The density functional theory studies revealed that in the (1-4)b complexes, the C-carbene-Pd sigma-bonding interaction was significantly stronger than the trans Pd-N-pyridine sigma-bonding interaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.01.062