N-methyl-2,5-di(4-trifluoromethylphenyl)pyrrole | 1227480-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-methyl-2,5-di(4-trifluoromethylphenyl)pyrrole
• 英文别名: 1-methyl-2,5-bis(4-(trifluoromethyl)phenyl)pyrrole；2,5-bis(4-trifluoromethylphenyl)-N-methylpyrrole；1-Methyl-2,5-bis[4-(trifluoromethyl)phenyl]pyrrole
• CAS: 1227480-10-5
• 化学式: C₁₉H₁₃F₆N
• 分子量: 369.309
• InChiKey: CKXAKPBIPHTBCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 4-碘三氟甲苯 在 [Pd(1,10-phenanthroline)₂](PF₆)₂ 、 caesium carbonate 作用下， 以 二甲胺 为溶剂， 反应 12.0h， 以79%的产率得到N-methyl-2,5-di(4-trifluoromethylphenyl)pyrrole
  参考文献：
  名称：

  Direct multiple C–H bond arylation reaction of heteroarenes catalyzed by cationic palladium complex bearing 1,10-phenanthroline

  摘要：

  一种带有1,10-菲咯啉配体的阳离子钯络合物被发现能够催化杂环芳烃与芳基碘化物的直接C–H芳香化反应，从而选择性地生成单芳基、双芳基或三芳基产物。

  DOI：

  10.1039/b920794e

文献信息

• Synthesis of 2,5-Diarylpyrroles by Ligand-Free Palladium-Catalyzed CH Activation of Pyrroles in Ionic Liquids
  作者：Peter Ehlers、Andranik Petrosyan、Jens Baumgard、Stefan Jopp、Norbert Steinfeld、Tariel V. Ghochikyan、Ashot S. Saghyan、Christine Fischer、Peter Langer

  DOI：10.1002/cctc.201300099

  日期：2013.8

  The palladium‐catalyzed CH activation and arylation of N‐methylpyrrole and N‐phenylpyrrole allowed a convenient synthesis of diarylpyrroles. The reactions were performed by using tetrabutylammonium acetate as an ionic solvent, which allowed for the application of a ligand‐free catalytic system by using simple palladium salts or polyvinylpyrrolidone‐stabilized palladium nanoparticles as the catalyst

  钯催化的CH活化和N-甲基吡咯和N-苯基吡咯的芳基化使得二芳基吡咯的合成方便。反应是通过使用乙酸四丁铵作为离子溶剂进行的，该反应可以通过使用简单的钯盐或聚乙烯吡咯烷酮稳定的钯纳米颗粒作为催化剂来应用无配体的催化体系。
• Palladium-Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners
  作者：Rongwei Jin、Kedong Yuan、Emmanuelle Chatelain、Jean-François Soulé、Henri Doucet

  DOI：10.1002/adsc.201400736

  日期：2014.12.15

  AbstractThe reactivity of pyrrole derivatives for palladium‐catalysed desulfitative arylation has been investigated. 1‐Methyl‐, 1‐phenyl‐ and 1‐benzylpyrroles were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine‐free catalyst. Highly regioselective arylations at carbon C2 of pyrroles were observed in all cases. A wide variety of substituents on the benzenesulfonyl derivative was tolerated.It should be noted that even bromo‐ and iodo‐benzenesulfonyl chlorides were successfully coupled with pyrrole derivatives without cleavage of the CBr or CI bonds, allowing further transformations. Surprisingly, with indoles, mixtures of C2‐ and C3‐arylation products were obtained.magnified image