2-(2,2-dibromovinyl)-4-iodoaniline | 1240045-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2,2-dibromovinyl)-4-iodoaniline
• 英文别名: 2-(2,2-Dibromoethenyl)-4-iodoaniline
• CAS: 1240045-32-2
• 化学式: C₈H₆Br₂IN
• 分子量: 402.855
• InChiKey: YQKLKZHLHLKWTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,2-dibromovinyl)-4-iodoaniline 在 palladium diacetate 、 potassium carbonate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 14.08h， 以68%的产率得到2-bromo-5-iodo-1H-indole
  参考文献：
  名称：

  The Role of Reversible Oxidative Addition in Selective Palladium(0)-Catalyzed Intramolecular Cross-Couplings of Polyhalogenated Substrates: Synthesis of Brominated Indoles

  摘要：

  A Pd(0)-catalyzed C-N bond-forming reaction leading to the synthesis of brominated indoles is described. The use of the phosphine ligand PtBu3 is necessary for reactivity. It is proposed that the bulky ligand serves to prevent inhibition of the catalyst by facilitating reversible oxidative addition into the product C-Br bond. Intramolecular coupling of a vinyl bromide in the presence of an aryl iodide can take place, demonstrating unprecedented levels of selectivity.

  DOI：

  10.1021/ja1052335
• 作为产物：
  描述：

  2-(2,2-二溴乙烯基)苯胺 在 双氧水 、 溶剂黄146 、 potassium iodide 作用下， 生成 2-(2,2-dibromovinyl)-4-iodoaniline
  参考文献：
  名称：

  The Role of Reversible Oxidative Addition in Selective Palladium(0)-Catalyzed Intramolecular Cross-Couplings of Polyhalogenated Substrates: Synthesis of Brominated Indoles

  摘要：

  A Pd(0)-catalyzed C-N bond-forming reaction leading to the synthesis of brominated indoles is described. The use of the phosphine ligand PtBu3 is necessary for reactivity. It is proposed that the bulky ligand serves to prevent inhibition of the catalyst by facilitating reversible oxidative addition into the product C-Br bond. Intramolecular coupling of a vinyl bromide in the presence of an aryl iodide can take place, demonstrating unprecedented levels of selectivity.

  DOI：

  10.1021/ja1052335

文献信息

• The Role of Reversible Oxidative Addition in Selective Palladium(0)-Catalyzed Intramolecular Cross-Couplings of Polyhalogenated Substrates: Synthesis of Brominated Indoles
  作者：Stephen G. Newman、Mark Lautens

  DOI：10.1021/ja1052335

  日期：2010.8.25

  A Pd(0)-catalyzed C-N bond-forming reaction leading to the synthesis of brominated indoles is described. The use of the phosphine ligand PtBu3 is necessary for reactivity. It is proposed that the bulky ligand serves to prevent inhibition of the catalyst by facilitating reversible oxidative addition into the product C-Br bond. Intramolecular coupling of a vinyl bromide in the presence of an aryl iodide can take place, demonstrating unprecedented levels of selectivity.