tert-butyl 2-(benzo[d]oxazol-2-yl)-1H-pyrrole-1-carboxylate | 1251914-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: tert-butyl 2-(benzo[d]oxazol-2-yl)-1H-pyrrole-1-carboxylate
• CAS: 1251914-13-2
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: NHFJTDWWDIBGRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.26
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-氯苯并恶唑 、 1-Boc-吡咯-2-硼酸 在 potassium phosphate 、 XPhos Pd G2 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以93%的产率得到tert-butyl 2-(benzo[d]oxazol-2-yl)-1H-pyrrole-1-carboxylate
  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