1-(4-fluorophenyl)-4-(thiophen-2-yl)-1H-pyrazole | 1251914-10-9

• 英文名称: 1-(4-fluorophenyl)-4-(thiophen-2-yl)-1H-pyrazole
• 英文别名: 1-(4-Fluorophenyl)-4-thiophen-2-ylpyrazole
• CAS: 1251914-10-9
• 化学式: C₁₃H₉FN₂S
• 分子量: 244.292
• InChiKey: HPDARABTMRWJLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩硼酸 、 4-溴-1-(4-氟苯基)-1H-吡唑 在 potassium phosphate 、 XPhos Pd G2 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以89%的产率得到1-(4-fluorophenyl)-4-(thiophen-2-yl)-1H-pyrazole
  参考文献：
  名称：

  A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids

  摘要：

  Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 degrees C in short reaction times to give the desired products in excellent yields.

  DOI：

  10.1021/ja1073799