4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)phenol

• 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-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)phenol
• 化学式: C₁₁H₁₁BrN₂O
• 分子量: 267.125
• InChiKey: INQMVUPWQSUBRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)phenol 、 palladium diacetate 以 乙醇 为溶剂， 反应 12.0h， 以86%的产率得到bis[4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)phenolato]palladium(II)
  参考文献：
  名称：

  Cyclometallation, steric and electronic tendencies in a series of Pd(II) complex pre-catalysts bearing imidazole–phenol ligands and effects on Suzuki–Miyaura catalytic efficiencies

  摘要：

  A series of new structurally and electronically diversified palladium complexes derived from seven less sterically crowded 2-(4,5-diinethyl-1H-imidazol-2-yl) pheno1/2-(4,5-diethyl-1H-imidazol-2-yl) phenol ligands and fourteen 2-(4,5-diphenyl-1H-imidazol-2-yl) phenols/2-(1H-phenanthro[9,10-d]imidazol-2-yl) phenols bearing varying degrees of higher steric bulk have been prepared and characterized. While single crystals grown from precipitated products of complexation reactions confirmed the bis-ligand Pd(NO)(2) coordination, few crystals obtained from reaction filtrates involving the 244,5-diphenyl-1H-imidazol-2-yl) phenols provided evidence for formation of N (O) over cap(C) over cap chelation species achieved by cyclometallation. Results from structural analyses and catalytic outcomes generally indicate that desirable variables on the ligand frameworks for obtaining superior catalyst activities either provides hemilabile or sterically strained chelation characters, which would both favour generation of monodentate coordination species at the catalysis temperature. In particular, correlation was observed between tendency for cyclometallation in the palladium complexes and poor Suzuki-Miyaura catalytic prospects. Based on hopeful activity obtained for the complex bearing 4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl) phenol, it was also concluded that sterically bulky ligand is not a necessity for high coupling efficiency, while presence of potentially cyclometallating substituent moieties in the vicinity of the palladium centre may in fact destroy catalytic prospects. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.06.001
• 作为产物：
  描述：

  2,3-丁二酮 、 5-溴水杨醛 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以23%的产率得到4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)phenol
  参考文献：
  名称：

  Cyclometallation, steric and electronic tendencies in a series of Pd(II) complex pre-catalysts bearing imidazole–phenol ligands and effects on Suzuki–Miyaura catalytic efficiencies

  摘要：

  A series of new structurally and electronically diversified palladium complexes derived from seven less sterically crowded 2-(4,5-diinethyl-1H-imidazol-2-yl) pheno1/2-(4,5-diethyl-1H-imidazol-2-yl) phenol ligands and fourteen 2-(4,5-diphenyl-1H-imidazol-2-yl) phenols/2-(1H-phenanthro[9,10-d]imidazol-2-yl) phenols bearing varying degrees of higher steric bulk have been prepared and characterized. While single crystals grown from precipitated products of complexation reactions confirmed the bis-ligand Pd(NO)(2) coordination, few crystals obtained from reaction filtrates involving the 244,5-diphenyl-1H-imidazol-2-yl) phenols provided evidence for formation of N (O) over cap(C) over cap chelation species achieved by cyclometallation. Results from structural analyses and catalytic outcomes generally indicate that desirable variables on the ligand frameworks for obtaining superior catalyst activities either provides hemilabile or sterically strained chelation characters, which would both favour generation of monodentate coordination species at the catalysis temperature. In particular, correlation was observed between tendency for cyclometallation in the palladium complexes and poor Suzuki-Miyaura catalytic prospects. Based on hopeful activity obtained for the complex bearing 4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl) phenol, it was also concluded that sterically bulky ligand is not a necessity for high coupling efficiency, while presence of potentially cyclometallating substituent moieties in the vicinity of the palladium centre may in fact destroy catalytic prospects. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.06.001