1-ethyl-4-iodo-2,3,5-trimethylpyrazolium iodide | 934838-64-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-ethyl-4-iodo-2,3,5-trimethylpyrazolium iodide
• CAS: 934838-64-9
• 化学式: C₈H₁₄IN₂*I
• 分子量: 392.022
• InChiKey: ABKWLIHGVDDDTR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.44
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-ethyl-4-iodo-2,3,5-trimethylpyrazolium iodide 以 二氯甲烷 为溶剂， 生成 bis(μ-iodo)bis(cyclohexyl C-imino)diiododipalladium(II)
  参考文献：
  名称：

  Reactivity Differences of Palladium(II) Dimers Bearing Heterocyclic Carbenes with Two, One, or No α-Nitrogen Atoms toward Isocyanides

  摘要：

  Pd(II) dimers [PdI2(rNHC)](2) (1a,b) of pyrazole-based remote N-heterocyclic carbenes (rNHCs) have been synthesized through oxidative addition of 4-iodopyrazolium iodides (A, B) to [Pd-2(dba)(3)]. Reaction of I a with aromatic (CN-Xyl) or aliphatic (CN-Cy) isocyanides led to the template-assisted formation of novel Pd(II) dimers 8 and 9 bearing betainic C-imino ligands via isocyanide insertion into Pd-C-rNHC bonds and subsequent dimerization. In contrast, both isocyanides reacted with the dimers [PdI2(Me-2-indy)](2) (2) and [PdI2(Me-2-bimy)](2) (3) bearing indazolin-3-ylidenes and benzimidazolin-2-ylidenes with formation of mononuclear mixed carbene/isocyanide complexes 4-7. Notably, only dimer 8 underwent further bridge cleavage with excess isocyanide, yielding the mixed C-imino/CN-Xyl complex 10, while dimer 9 remained intact. These results highlight the uniquely different reactivities of complexes with carbenes having no a-nitrogen versus those with one or two a-nitrogen atoms, as a result of their decreasing donor abilities.

  DOI：

  10.1021/om101169x

文献信息

• Preparation and characterization of the first pyrazole-based remote N-heterocyclic carbene complexes of palladium(ii)
  作者：Yuan Han、Han Vinh Huynh

  DOI：10.1039/b615441g

  日期：——

  The first pyrazolin-4-ylidene complexes of palladium(II) have been synthesized by oxidative addition of 4-iodopyrazolium salts to Pd2(dba)3/PPh3 and were fully characterized by multinuclear NMR spectroscopies, ESI mass spectrometry and X-ray diffraction studies.

  通过将 4-iodopyrazolium 盐氧化加入 Pd2(dba)3/PPh3 合成了首批吡唑啉-4-亚基钯（II）配合物，并通过多核核磁共振光谱、ESI 质谱和 X 射线衍射研究对其进行了全面表征。
• Palladium(II) Pyrazolin-4-ylidenes: Remote N-Heterocyclic Carbene Complexes and Their Catalytic Application in Aqueous Suzuki−Miyaura Coupling
  作者：Yuan Han、Han Vinh Huynh、Geok Kheng Tan

  DOI：10.1021/om7009107

  日期：2007.12.1

  Two monocationic complexes of pyrazole-derived remote carbene ligands of the type trans-[PdI(rNHC)(PPh3)2]+OTf– rNHC = 2-ethyl-3,5-dimethyl-1-phenylpyrazolin-4-ylidene (6a), 1-ethyl-2,3,5-trimethylpyrazolin-4-ylidene (6b)} were prepared by oxidative addition of 4-iodo-1,2,3,5-tetrasubstituted pyrazolium triflate salts to [Pd2(dba)3]/PPh3 in good yields. Both compounds were fully characterized by multinuclei

  的类型的吡唑衍生的远程碳烯配体的两个单阳离子络合物的反式[PDI（RNHC）（PPH - 3）2 ] +光学传递函数- RNHC = 2-乙基-3,5-二甲基-1-苯基吡唑-4-亚基（在图6a）中，通过将4-碘-1,2,3,5-四取代的三氟甲磺酸吡唑鎓盐氧化添加至[Pd 2（dba ），制备了1-乙基-2,3,5-三甲基吡唑啉-4-亚烷基（6b）}。）3 ] / PPh 3丰产。两种化合物均通过多核NMR光谱，电喷雾电离质谱和X射线衍射分析得到了充分表征。对这些阳离子配合物与先前报道的中性对应物的Suzuki-Miyaura水溶液的催化活性的比较研究揭示了前者的优越性。