4-((1-tert-butyl)-1H-imidazolium-3-yl)methyl-1-(2,6-diisopropylphenyl)-3-methyl-1H-1,2,3-triazol-3-ium bromide trifluoromethanesulfonate | 1392271-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-((1-tert-butyl)-1H-imidazolium-3-yl)methyl-1-(2,6-diisopropylphenyl)-3-methyl-1H-1,2,3-triazol-3-ium bromide trifluoromethanesulfonate
• CAS: 1392271-00-9
• 化学式: Br*CF₃O₃S*C₂₃H₃₅N₅
• 分子量: 610.539
• InChiKey: XYLNPAWGZKKTDJ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  87.71
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-((1-tert-butyl)-1H-imidazolium-3-yl)methyl-1-(2,6-diisopropylphenyl)-3-methyl-1H-1,2,3-triazol-3-ium bromide trifluoromethanesulfonate 以 乙腈 为溶剂， 反应 5.17h， 生成 trans-[PdI₂(triethylphosphine)(κ¹-^tBuImTrz(H)^Me_Dipp)][I]
  参考文献：
  名称：

  Unsymmetrical Dicarbenes Based on N-Heterocyclic/Mesoionic Carbene Frameworks: A Stepwise Metalation Strategy for the Generation of a Dicarbene-Bridged Mixed-Metal Pd/Rh Complex

  摘要：

  A pair of linked imidazolium/triazolium salts have been prepared using copper-catalyzed azide-alkyne cycloaddition (CuAAC or "click" chemistry) and methylation protocols, producing a precursor for bidentate N-heterocyclic carbene (NHC)/mesoionic carbene (MIC) ligands, representing a rare example of an NHC/MIC hybrid. Metalation of one-half of this dicationic species using the basic ligand-containing [Pd(OAc)(2)] in the presence of potassium iodide or half an equivalent of [Rh(mu-OMe) (COD)](2) yields NHC-anchored/pendent triazolium species of Pd or Rh, respectively. The pendent Pd species can be further functionalized through iodide substitution by various monophosphines, which preferentially adopt a cis or trans arrangement depending on the bulk of the anchored NHC substituent. Combining these "internal-base" and "pendent" strategies, the pendent MIC(H)(+) arm of the trans-triethylphosphinefunctionalized Pd species can be metalated by [Rh(mu-OMe)(COD)](2), resulting in the generation of a hybrid NHC/MIC-bridged mixed-metal Pd/Rh species. This complex represents the first example of a hybrid unsymmetrical dicarbene bridging two different metals.

  DOI：

  10.1021/om3004543
• 作为产物：
  描述：

  1-(tert-butyl)-3-prop-2-yn-1-yl-1H-imidazolium bromide 在 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 4-((1-tert-butyl)-1H-imidazolium-3-yl)methyl-1-(2,6-diisopropylphenyl)-3-methyl-1H-1,2,3-triazol-3-ium bromide trifluoromethanesulfonate
  参考文献：
  名称：

  Unsymmetrical Dicarbenes Based on N-Heterocyclic/Mesoionic Carbene Frameworks: A Stepwise Metalation Strategy for the Generation of a Dicarbene-Bridged Mixed-Metal Pd/Rh Complex

  摘要：

  A pair of linked imidazolium/triazolium salts have been prepared using copper-catalyzed azide-alkyne cycloaddition (CuAAC or "click" chemistry) and methylation protocols, producing a precursor for bidentate N-heterocyclic carbene (NHC)/mesoionic carbene (MIC) ligands, representing a rare example of an NHC/MIC hybrid. Metalation of one-half of this dicationic species using the basic ligand-containing [Pd(OAc)(2)] in the presence of potassium iodide or half an equivalent of [Rh(mu-OMe) (COD)](2) yields NHC-anchored/pendent triazolium species of Pd or Rh, respectively. The pendent Pd species can be further functionalized through iodide substitution by various monophosphines, which preferentially adopt a cis or trans arrangement depending on the bulk of the anchored NHC substituent. Combining these "internal-base" and "pendent" strategies, the pendent MIC(H)(+) arm of the trans-triethylphosphinefunctionalized Pd species can be metalated by [Rh(mu-OMe)(COD)](2), resulting in the generation of a hybrid NHC/MIC-bridged mixed-metal Pd/Rh species. This complex represents the first example of a hybrid unsymmetrical dicarbene bridging two different metals.

  DOI：

  10.1021/om3004543