2-(4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl)pyridine | 1318079-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl)pyridine
• 英文别名: 2-[4-(4-Phenyltriazol-1-yl)phenyl]pyridine；2-[4-(4-phenyltriazol-1-yl)phenyl]pyridine
• CAS: 1318079-64-9
• 化学式: C₁₉H₁₄N₄
• 分子量: 298.347
• InChiKey: XHUDTTGCNIKKEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴苯基三氟硼酸钾 在 四(三苯基膦)钯 、 sodium azide 、 caesium carbonate 、 copper(I) bromide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 11.5h， 生成 2-(4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl)pyridine
  参考文献：
  名称：

  Efficient and rapid synthesis of regioselective functionalized potassium 1,2,3-triazoletrifluoroborates via 1,3-dipolar cycloaddition

  摘要：

  In this study, we present a previously unreported method of preparing regiospecific organo-[1,2,3]-triazol-1-aryl-trifluoroborates from haloaryltrifluoroborates via a one-pot 1,3-dipolar cycloaddition reaction. We found that the use of either electron-rich or electron-deficient haloaryltrifluoroborates led to the desired cycloaddition products with good to excellent yields. Furthermore, we successfully carried Out the cross-coupling reactions of the obtained triazoles with various aryl halides by means of the Suzuki-Miyaura reaction in the presence of 3 mol % of Pd(PPh(3))(4) catalyst in a 20% aqueous 1,4-dioxane solution at 100 degrees C; all these reactions yielded complete conversion to the corresponding products. Besides providing a high level of personnel safety, our highly versatile approach allows the preparation of functionalized organotrifluoborates containing 1,2,3-triazoles with retained functionality. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.126

文献信息

• Efficient and rapid synthesis of regioselective functionalized potassium 1,2,3-triazoletrifluoroborates via 1,3-dipolar cycloaddition
  作者：Krishnavenu Bolla、Taejung Kim、Jung Ho Song、Seokjoon Lee、Jungyeob Ham

  DOI：10.1016/j.tet.2011.05.126

  日期：2011.8

  In this study, we present a previously unreported method of preparing regiospecific organo-[1,2,3]-triazol-1-aryl-trifluoroborates from haloaryltrifluoroborates via a one-pot 1,3-dipolar cycloaddition reaction. We found that the use of either electron-rich or electron-deficient haloaryltrifluoroborates led to the desired cycloaddition products with good to excellent yields. Furthermore, we successfully carried Out the cross-coupling reactions of the obtained triazoles with various aryl halides by means of the Suzuki-Miyaura reaction in the presence of 3 mol % of Pd(PPh(3))(4) catalyst in a 20% aqueous 1,4-dioxane solution at 100 degrees C; all these reactions yielded complete conversion to the corresponding products. Besides providing a high level of personnel safety, our highly versatile approach allows the preparation of functionalized organotrifluoborates containing 1,2,3-triazoles with retained functionality. (C) 2011 Elsevier Ltd. All rights reserved.