1,3-bis-(3,4,5-trimethoxybenzyl)benzimidazolium chloride | 1009630-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1,3-bis-(3,4,5-trimethoxybenzyl)benzimidazolium chloride
• CAS: 1009630-16-3
• 化学式: C₂₇H₃₁N₂O₆*Cl
• 分子量: 515.006
• InChiKey: VNCLUYBVKVHBFO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.19
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3-bis-(3,4,5-trimethoxybenzyl)benzimidazolium chloride 、 methoxy(cyclooctadiene)rhodium(I) dimer 以 四氢呋喃 为溶剂， 反应 5.0h， 以67%的产率得到1,3-bis[(3,4,5-trimethoxybenzyl)]-benzimidazolin-2-ylidene-[(1,2,5,6-η⁴)-1,5-cyclooctadiene]chlororhodium(I)
  参考文献：
  名称：

  Synthesis of rhodium complexes derived from benzimidazolin-2-ylidene ligands and first used for the addition of arylboron to benzonitriles

  摘要：

  Benzimidazolium salts and their new rhodium complexes ([RH(COD)(NHC)Cl]) were synthesized and characterized by elemental analysis, H-1 NMR, C-13 NMR, and IR spectroscopy. The addition of arylboron to benzonitriles in the presence of a catalytic amount of rhodium NHC complexes was examined. Corresponding carbonyl compounds were obtained in good yields. This method allows for the preparation of a wide variety of carbonyl compounds in moderate to excellent yields and displays a high level of activity for the addition of arylboron to nitriles. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.01.025
• 作为产物：
  描述：

  、 原甲酸三乙酯 在 氯化铵 作用下， 以90%的产率得到1,3-bis-(3,4,5-trimethoxybenzyl)benzimidazolium chloride
  参考文献：
  名称：

  苄基咪唑啉鎓、3,4,5,6-四氢嘧啶鎓和苯并咪唑鎓盐：在钌催化的烯丙基取代反应中的应用

  摘要：

  制备了咪唑啉鎓、四氢嘧啶鎓和苯并咪唑鎓盐。与 tBuOK 反应后，它们会生成卡宾配体，这些配体与 [RuCp*(MeCN)3]PF6 原位结合以产生钌催化剂，该催化剂对于丙二酸二甲酯作为亲碳试剂和苯酚取代烯丙基底物具有活性。研究了 N-杂环结构以及苄基 N-取代基对反应性和区域选择性的影响。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200800007

文献信息

• Direct Arylation of Arene C−H Bonds by Cooperative Action of NHCarbene−Ruthenium(II) Catalyst and Carbonate via Proton Abstraction Mechanism
  作者：Ismail Özdemir、Serpil Demir、Bekir Çetinkaya、Christophe Gourlaouen、Feliu Maseras、Christian Bruneau、Pierre H. Dixneuf

  DOI：10.1021/ja710276x

  日期：2008.1.30

  Direct functionalization of sp(2) C-H bonds via ortho diarylation of 2-pyridyl benzene with arylbromides was achieved using ruthenium(II) catalysts containing a RuCl2(NHC) unit and generated from [RuCl2(arene)](2) and two types of NHC precursors, pyrimidinium and benzimidazolium salts, in the presence of Cs2CO3. DFT calculations from RuCl2(NHC)(2-pyridylbenzene) show that a proton abstraction mechanism, on cooperative actions of both the coordinated base and the Ru(II) center, is favoured via a 13.7 kcal mol(-1) exothermic process affording an orthometalated intermediate with a 2.009 angstrom Ru-C bond.