(6-bromopyridyn-3-yl)(2,4,6-triisopropylphenyl)iodonium triflate | 1038998-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (6-bromopyridyn-3-yl)(2,4,6-triisopropylphenyl)iodonium triflate
• CAS: 1038998-06-9
• 化学式: CF₃O₃S*C₂₀H₂₆BrIN
• 分子量: 636.312
• InChiKey: ATDNOWOTZWYDPO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  70.09
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-甲基吲哚 、 (6-bromopyridyn-3-yl)(2,4,6-triisopropylphenyl)iodonium triflate 在 2,6-二叔丁基吡啶 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以38%的产率得到3-(6-bromopyridin-3-yl)-1-methyl-1H-indole
  参考文献：
  名称：

  Cu(II)-Catalyzed Direct and Site-Selective Arylation of Indoles Under Mild Conditions

  摘要：

  We have developed a new site-selective Cu(II)-catalyzed C-H bond funtionalization process that can selectively arlate indoles at either the C3 or C2 position under miled conditions. The scope of arylation process is broad and tolerates broad functionality on both indole and aryl unit, which makes it amenable to further elaboartion. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl that undergoes intial addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group of C3 to C2, and this can be controlled by the nature of the group on the nitrogen atm; free (NH)-and N-alkylindoles deliver the C3-arylated product, whereas N-acytylindoles affored the C2 isomer, both with excellent yield and selectivity.

  DOI：

  10.1021/ja801767s
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 (6-bromopyridyn-3-yl)(2,4,6-triisopropylphenyl)iodonium tetrafluoroborate 以 乙腈 为溶剂， 反应 15.0h， 以91%的产率得到(6-bromopyridyn-3-yl)(2,4,6-triisopropylphenyl)iodonium triflate
  参考文献：
  名称：

  Cu(II)-Catalyzed Direct and Site-Selective Arylation of Indoles Under Mild Conditions

  摘要：

  We have developed a new site-selective Cu(II)-catalyzed C-H bond funtionalization process that can selectively arlate indoles at either the C3 or C2 position under miled conditions. The scope of arylation process is broad and tolerates broad functionality on both indole and aryl unit, which makes it amenable to further elaboartion. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl that undergoes intial addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group of C3 to C2, and this can be controlled by the nature of the group on the nitrogen atm; free (NH)-and N-alkylindoles deliver the C3-arylated product, whereas N-acytylindoles affored the C2 isomer, both with excellent yield and selectivity.

  DOI：

  10.1021/ja801767s