[1,3-di((4−2,6-diisopropylphenyl)-1H-1,2,3-triazolyl)-methylene-imidazolium]bromide | 1588950-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [1,3-di((4−2,6-diisopropylphenyl)-1H-1,2,3-triazolyl)-methylene-imidazolium]bromide
• 英文别名: [1,3-di((4-2,6-diisopropylphenyl)-1H-1,2,3-triazolyl)-methylene-imidazolium]bromide
• CAS: 1588950-55-3
• 化学式: Br*C₃₃H₄₃N₈
• 分子量: 631.662
• InChiKey: JBNFNRJJCYTFSW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70.23
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  bis(η3-allyl-μ-chloropalladium(II)) 、 [1,3-di((4−2,6-diisopropylphenyl)-1H-1,2,3-triazolyl)-methylene-imidazolium]bromide 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以64%的产率得到palladium(η³-allyl)chlorido(1,3-di-((4-2,6-diisopropylphenyl)-1H-1,2,3-triazolyl)methylene-imidazol-ylidene)
  参考文献：
  名称：

  Convenient Transfer Semihydrogenation Methodology for Alkynes Using a Pd^II-NHC Precatalyst

  摘要：

  A convenient and easy-to-use protocol for the Z-selective transfer semihydrogenation of alkynes was developed, using ammonium formate as the hydrogen source and the easily prepared and commercially available, highly stable complex PdC1(eta(3)-C3H5)(IMes) (1) as the (pre)catalyst. Combined with triphenyl posphine as an additional ligand, this system provides a robust catalytic synthetic method that shows little to no over-reduction or isomerization after full substrate conversion. The system allows the direct use of solvents and reagents, as received from the supplier without drying or purification, thus providing a practical method for semihydrogenation of a broad range of alkynes. The mechanism behind these high and enhanced selectivities was determined through a set of kinetic experiments.

  DOI：

  10.1021/cs4011502
• 作为产物：
  描述：

  2,6-diisopropyl-1-azidobenzene 、 1,3-dipropargylimidazolium bromide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 168.0h， 以62%的产率得到[1,3-di((4−2,6-diisopropylphenyl)-1H-1,2,3-triazolyl)-methylene-imidazolium]bromide
  参考文献：
  名称：

  Convenient Transfer Semihydrogenation Methodology for Alkynes Using a Pd^II-NHC Precatalyst

  摘要：

  A convenient and easy-to-use protocol for the Z-selective transfer semihydrogenation of alkynes was developed, using ammonium formate as the hydrogen source and the easily prepared and commercially available, highly stable complex PdC1(eta(3)-C3H5)(IMes) (1) as the (pre)catalyst. Combined with triphenyl posphine as an additional ligand, this system provides a robust catalytic synthetic method that shows little to no over-reduction or isomerization after full substrate conversion. The system allows the direct use of solvents and reagents, as received from the supplier without drying or purification, thus providing a practical method for semihydrogenation of a broad range of alkynes. The mechanism behind these high and enhanced selectivities was determined through a set of kinetic experiments.

  DOI：

  10.1021/cs4011502