5-(2,6-difluorophenyl)-2-methylbenzo[d]thiazole | 1251913-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-(2,6-difluorophenyl)-2-methylbenzo[d]thiazole
• 英文别名: 5-(2,6-difluorophenyl)-2-methylbenzothiazole；5-(2,6-Difluorophenyl)-2-methyl-1,3-benzothiazole
• CAS: 1251913-98-0
• 化学式: C₁₄H₉F₂NS
• 分子量: 261.295
• InChiKey: KNICHYNGRATIGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氯-2-甲基苯并噻唑 、 2,6-二氟苯硼酸 在 potassium phosphate 、 XPhos Pd G2 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以99%的产率得到5-(2,6-difluorophenyl)-2-methylbenzo[d]thiazole
  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

文献信息

• <i>N</i>-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
  作者：Nicholas C. Bruno、Nootaree Niljianskul、Stephen L. Buchwald

  DOI：10.1021/jo500355k

  日期：2014.5.2

  A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free -NH2 group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki-Miyaura and C-N cross-coupling reactions.