4-methyl-4′-(tributylstannyl)azobenzene | 1556876-58-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: 4-methyl-4′-(tributylstannyl)azobenzene
• CAS: 1556876-58-4
• 化学式: C₂₅H₃₈N₂Sn
• 分子量: 485.3
• InChiKey: YSGNANZRUSCQCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.37
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-4′-(tributylstannyl)azobenzene 、 1-溴-4-硝基苯 在 四(三苯基膦)钯 、 copper(l) chloride 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以71%的产率得到4-(4-nitrophenyl)-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
• 作为产物：
  描述：

  乙烷,三氯氟- 在 四(三苯基膦)钯 、 potassium peroxomonosulphate 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 20.58h， 生成 4-methyl-4′-(tributylstannyl)azobenzene
  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