1-(p-toluenesulfonyl)-6-(2-methoxyphenyl)indole

• 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: 1-(p-toluenesulfonyl)-6-(2-methoxyphenyl)indole
• 英文别名: 6-(2-methoxyphenyl)-1-tosyl-1H-indole；6-(2-Methoxyphenyl)-1-(4-methylphenyl)sulfonylindole
• 化学式: C₂₂H₁₉NO₃S
• 分子量: 377.464
• InChiKey: YQRJUXRZMCZEHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴-1-甲苯磺酰-1H-吲哚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 120.0h， 生成 1-(p-toluenesulfonyl)-6-(2-methoxyphenyl)indole
  参考文献：
  名称：

  Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection

  摘要：

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.

  DOI：

  10.1021/jo0491612

文献信息

• A one-pot “back-to-front” approach for the synthesis of benzene ring substituted indoles using allylboronic acids
  作者：Ganesh Karan、Samrat Sahu、Modhu Sudan Maji

  DOI：10.1039/d1cc01512e

  日期：——

  Synthesis of only benzene ring functionalized indoles and poly-substituted carbazoles is reported via a one-pot triple cascade benzannulation protocol. Usage of differently substituted and readily accessible allylboronic acids as a 3-carbon annulating partner enables diverse aliphatic and aromatic substitution patterns, which is still a daunting task. This scalable synthetic protocol tolerates broad

  通过一锅三重级联苯环化方案报道了仅苯环官能化的吲哚和多取代的咔唑的合成。使用不同取代和易于获得的烯丙基硼酸作为3碳环化伙伴可以实现多种脂族和芳族取代模式，这仍然是一项艰巨的任务。这种可扩展的合成协议具有宽泛的范围，因此可以进行进一步的下游修改。作为一种应用，合成了咔唑类天然产物糖唑啉和糖唑啉醇。
• Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection
  作者：Mònica Prieto、Esther Zurita、Esmeralda Rosa、Lourdes Muñoz、Paul Lloyd-Williams、Ernest Giralt

  DOI：10.1021/jo0491612

  日期：2004.10.1

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.