| 1416353-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• CAS: 1416353-42-8
• 化学式: C₃₁H₂₀N₂O₂
• 分子量: 452.512
• InChiKey: VWQNRTMWVOULDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-碘吡啶 在 palladium diacetate 、 铜 、 potassium carbonate 、 silver nitrate 、 对苯醌 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 54.0h， 生成 1-(4-formylphenyl)-9-(pyridin-2-yl)-9H-carbazole 、
  参考文献：
  名称：

  Direct Ortho Arylation of 9-(Pyridin-2-yl)-9H-carbazoles Bearing a Removable Directing Group via Palladium(II)-Catalyzed C–H Bond Activation

  摘要：

  A one-pot synthesis of ortho-arylated 9-(pyridin-2-yl)-9H-carbazoles via C-H bond activation is presented. Silver nitrate and tert-butyl alcohol were found to be the best oxidant and solvent for the process, respectively. The product yields are from modest to excellent, and the reaction showed sufficient functional group tolerance. p-Benzoquinone served as an important ligand for the transmetalation and reductive elimination steps in the catalytic process. The key intermediate of the reaction, a 9-(pyridin-2-yl)-9H-carbazole palladacycle, was isolated, and its structure was unequivocally confirmed by X-ray crystallography. No kinetic isotope effect (k(H)/k(D) = 1.00 +/- 0.17) for the C-H bond activation step was observed. In addition, a Hammett experiment gave a negative rho value, -2.16 +/- 0.02. The directing group, pyridinyl, was demonstrated to be a removable functional group. Finally, a rational catalytic mechanism is presented on the basis of all experimental evidence.

  DOI：

  10.1021/om301071m