4-(5-methylcarboxylate-2-furanyl)-4′-methylazobenzene | 1556876-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-(5-methylcarboxylate-2-furanyl)-4′-methylazobenzene
• 英文别名: Methyl 5-[4-[(4-methylphenyl)diazenyl]phenyl]furan-2-carboxylate；methyl 5-[4-[(4-methylphenyl)diazenyl]phenyl]furan-2-carboxylate
• CAS: 1556876-16-4
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: QNIQJWKYBJNQJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-iodo-4’-methylazobenzene 在 四(三苯基膦)钯 、 copper(l) chloride 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.17h， 生成 4-(5-methylcarboxylate-2-furanyl)-4′-methylazobenzene
  参考文献：
  名称：

  Tin-Functionalized Azobenzenes as Nucleophiles in Stille Cross-Coupling Reactions

  摘要：

  The metalation of azobenzene by halogen-metal exchange typically leads to a reduction of the azo group to give hydrazine derivatives as major byproducts, instead of the desired metalated azobenzene species. In cross-coupling reactions, azobenzenes therefore usually serve as electrophiles, which greatly limits the scope of the reaction. To solve this problem, we have developed a mild and fast method to stannylate azobenzenes in high yields. This research shows that these stannylated azobenzenes can be used as nucleophilic components in Stille cross-coupling reactions with aryl bromides. The cross-coupling products were obtained in high yields ranging from 70 to 93%. With this reversal of the nucleophilic and electrophilic components, cross-coupling products are now accessible in which the aromatic rings coupled to the azobenzene bear functional groups that are sensitive to metalation.

  DOI：

  10.1021/jo402598u

文献信息

• Tin-Functionalized Azobenzenes as Nucleophiles in Stille Cross-Coupling Reactions
  作者：Jan Strueben、Paul J. Gates、Anne Staubitz

  DOI：10.1021/jo402598u

  日期：2014.2.21

  The metalation of azobenzene by halogen-metal exchange typically leads to a reduction of the azo group to give hydrazine derivatives as major byproducts, instead of the desired metalated azobenzene species. In cross-coupling reactions, azobenzenes therefore usually serve as electrophiles, which greatly limits the scope of the reaction. To solve this problem, we have developed a mild and fast method to stannylate azobenzenes in high yields. This research shows that these stannylated azobenzenes can be used as nucleophilic components in Stille cross-coupling reactions with aryl bromides. The cross-coupling products were obtained in high yields ranging from 70 to 93%. With this reversal of the nucleophilic and electrophilic components, cross-coupling products are now accessible in which the aromatic rings coupled to the azobenzene bear functional groups that are sensitive to metalation.