2,4,6-trifluoro-2'-methyl-biphenyl

• 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: 2,4,6-trifluoro-2'-methyl-biphenyl
• 英文别名: 1,3,5-Trifluoro-2-(2-methylphenyl)benzene；1,3,5-trifluoro-2-(2-methylphenyl)benzene
• 化学式: C₁₃H₉F₃
• 分子量: 222.21
• InChiKey: NZHQFJZLFSQDGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯甲苯 、 1,3,5-三氟苯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 potassium carbonate 作用下， 以 醋酸异丙酯 为溶剂， 反应 12.0h， 以82%的产率得到2,4,6-trifluoro-2'-methyl-biphenyl
  参考文献：
  名称：

  Mild and General Conditions for the Cross-Coupling of Aryl Halides with Pentafluorobenzene and Other Perfluoroaromatics

  摘要：

  New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.

  DOI：

  10.1021/ol0619967

文献信息

• Steric and electronic effects of arsa-Buchwald ligands on Suzuki–Miyaura coupling reaction
  作者：Akifumi Sumida、Kenta Ogawa、Hiroaki Imoto、Kensuke Naka

  DOI：10.1039/d2dt04139a

  日期：——

  arsa-Buchwald ligands, arsenic analogs of Buchwald ligands, and found that these ligands are effective for sterically hindered substrates because of facilitating the transmetalation step owing to the longer arsenic–palladium bond. However, the relationship between the structure and steric/electronic properties of the arsa-Buchwald ligands has not yet been studied in detail. In this study, a series of arsa-Buchwald

  铃木-宫浦偶联 (SMC) 反应是最常用的交叉偶联反应之一。庞大的联芳基二烷基单膦配体，即, Buchwald 配体，有利于 SMC 反应。我们最近开发了一种用于 arsa-Buchwald 配体（Buchwald 配体的砷类似物）的合成程序，并发现这些配体对空间位阻底物有效，因为较长的砷-钯键促进了金属转移步骤。然而，尚未详细研究 arsa-Buchwald 配体的结构和空间/电子特性之间的关系。在这项研究中，合成了一系列具有各种烷基取代基的 arsa-Buchwald 配体。环戊基为 SMC 反应提供了最高的催化活性，特别是对于空间位阻底物。此外，计算分析了 arsa-Buchwald 配体的空间/电子特性。
• Mild and General Conditions for the Cross-Coupling of Aryl Halides with Pentafluorobenzene and Other Perfluoroaromatics
  作者：Marc Lafrance、Daniel Shore、Keith Fagnou

  DOI：10.1021/ol0619967

  日期：2006.10.1

  New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.