1,3-bis[4-(4-{[3-(triethoxysilyl)propyl]thio}butyloxy)-2,6-diisopropylphenyl]imidazolium chloride | 1620922-82-8

• 分子结构分类: 有机化合物
• 英文名称: 1,3-bis[4-(4-{[3-(triethoxysilyl)propyl]thio}butyloxy)-2,6-diisopropylphenyl]imidazolium chloride
• CAS: 1620922-82-8
• 化学式: C₅₃H₉₃N₂O₈S₂Si₂*Cl
• 分子量: 1042.09
• InChiKey: ZFUOWUNCXXXLEN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  10.91
• 重原子数：
  68.0
• 可旋转键数：
  38.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  82.65
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  2,6-diisopropylnitrobenzene 在 甲酸 、 硫酸 、 安息香双甲醚 、 四丁基碘化铵 、 potassium carbonate 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 100.42h， 生成 1,3-bis[4-(4-{[3-(triethoxysilyl)propyl]thio}butyloxy)-2,6-diisopropylphenyl]imidazolium chloride
  参考文献：
  名称：

  功能化可烷氧基连接的N-杂环碳原子配体的模块化合成和用于布赫瓦尔德-哈特维格胺胺化的活性催化剂

  摘要：

  AbstractModular syntheses of functionalised, alkoxy‐tethered 1,3‐bis(2,4,6‐trimethylphenyl)imidazolium (IMes⋅H+) and 1,3‐bis(2,6‐diisopropylphenyl)imidazolium (IPr⋅H+) derivatives 1,3‐bis(4‐alkyloxy‐2,4,6‐trimethylphenyl)imidazolium (IXyOR⋅H+) and 1,3‐bis(4‐alkyloxy‐2,6‐diisopropylphenyl)imidazolium (IPrOR⋅H+) are reported. A reliable synthesis of the key starting material 4‐amino‐3,5‐diisopropylphenol is also described. Etherification of hydroxy‐decorated ligand intermediates before formation of the imidazolium core and subsequent modification, or direct etherification of the versatile synthon IPrOH⋅HCl, allowed access to various linker types including triethoxysilyl, primary amino and norbornenyl, which are not accessible by other methods. An IPrOR–palladium(II) complex was prepared, and its catalytic activity was evaluated in challenging Buchwald–Hartwig aminations of aryl chlorides. This precatalyst displayed excellent activity and selectivity under mild reaction conditions, achieving in some cases a 10‐fold improvement in TOF relative to the IPr‐based version. An unexpected activity profile was observed wherein sterically demanding anilines were coupled more easily than those lacking ortho‐substitution.magnified image

  DOI：

  10.1002/adsc.201300903

文献信息

• Heterogenization of Pd–NHC complexes onto a silica support and their application in Suzuki–Miyaura coupling under batch and continuous flow conditions
  作者：Alberto Martínez、Jamin L. Krinsky、Itziar Peñafiel、Sergio Castillón、Konstantin Loponov、Alexei Lapkin、Cyril Godard、Carmen Claver

  DOI：10.1039/c4cy00829d

  日期：——

  Immobilised Pd–NHC catalysts were successfully applied in Suzuki–Miyaura reaction under batch and flow conditions.

  固定化的Pd-NHC催化剂成功地应用于批量和流动条件下的Suzuki-Miyaura反应。