4-fluoro-2',4',6'-trimethyldiphenylamine | 1163303-73-8

• 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: 4-fluoro-2',4',6'-trimethyldiphenylamine
• 英文别名: N-(4-fluorophenyl)-2,4,6-trimethylaniline
• CAS: 1163303-73-8
• 化学式: C₁₅H₁₆FN
• 分子量: 229.297
• InChiKey: QWSROWMLEATRPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-1,3,5-三甲基苯 、 4-氟苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦 、 sodium t-butanolate 作用下， 以 邻二甲苯 为溶剂， 反应 12.0h， 以71%的产率得到4-fluoro-2',4',6'-trimethyldiphenylamine
  参考文献：
  名称：

  Effects of solvent and base on the palladium-catalyzed amination: PdCl2(Ph3P)2/Ph3P-catalyzed selective arylation of primary anilines with aryl bromides

  摘要：

  A readily accessible catalytic system, PdCl2(Ph3P)(2)/Ph3P, was developed for the selective arylation of primary anilines with aryl bromides. The strong influence of solvents and bases on the catalytic activity was observed. In refluxing o-xylene, triphenylphosphine shows high efficiency for Pd-catalyzed intermolecular amination reactions. By changing the bases, mono- and diarylation of primary amines could be selectively achieved in high yields. Moreover, the catalytic system showed good toleration for the steric hindrance of anilines. A series of N,N,N',N'-tetraaryl-1,1'-biphenyl-4,4'-diamines, important intermediates of OLED hole transport materials, were synthesized facilely via coupling reactions between 4,4'-diaminobiphenyls and aryl bromides. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.048

文献信息

• LIGANDS FOR METALS AS CATALYSTS FOR CARBON-CARBON BOND FORMATION
  申请人：LIANG Lan-Chang

  公开号：US20090163740A1

  公开（公告）日：2009-06-25

  The present invention provides a family of novel and stable ligands which chelate with a metal to form a complex. The ligand contains a t-butyl group or a ring, particularly a substituted aromatic group, linked to a nitrogen atom. The nitrogen atom further links to PR 1 R 2 , PR 1 R 2 R 9 , P(═O)R 1 R 2 , NR 1 R 2 , OR 1 , SR 1 , or AsR 1 R 2 group with a saturated or unsaturated hydrocarbon such that the structure of the ligand can be stabilized.

  本发明提供了一系列新颖且稳定的配体，这些配体与金属螯合形成复合物。该配体含有t-丁基基团或环，特别是取代芳基团，与氮原子连接。氮原子进一步与PR1R2、PR1R2R9、P(═O)R1R2、NR1R2、OR1、SR1或AsR1R2基团链接，带有饱和或不饱和的碳氢化合物，从而使配体的结构得以稳定。
• Synthesis of sterically encumbered di- and triarylamines by palladium-catalysed C–N coupling reactions under mild reaction conditions
  作者：Philipp Neigenfind、Daniel Knyszek、Jens Handelmann、Viktoria H. Gessner

  DOI：10.1039/d1cy02352g

  日期：——

  The synthesis of bulky, ortho-substituted triarylamines often represents a synthetic challenge, but is highly desirable due to the use of these compounds in organic electronics. Here, we report on a systematic study of the application of ylide-substituted phosphines (YPhos) in the Pd-catalysed formation of bulky di- and triarylamines. Screening of different ligands showed that whereas diarylation is

  大体积、邻位取代的三芳基胺的合成通常是一项合成挑战，但由于这些化合物在有机电子学中的应用，因此非常需要。在这里，我们报告了叶立德取代膦 (YPhos) 在 Pd 催化形成大体积二芳基胺和三芳基胺中的应用的系统研究。对不同配体的筛选表明，虽然大多数测试的 YPhos 配体都可以进行二芳基化，但三芳胺最有效地与最小、最灵活的 YPhos 配体 keYPhos 形成，在配体骨架中具有甲基基团。该配体允许在仅 60 °C 的低温下以良好至高产率合成一系列空间位阻二胺和三芳胺。优化的协议使最多三个三芳胺的邻位取代基，因此代表了一种方便而温和的合成方法。这通过合成用作有机电子材料的结构来证明。
• Effects of solvent and base on the palladium-catalyzed amination: PdCl2(Ph3P)2/Ph3P-catalyzed selective arylation of primary anilines with aryl bromides
  作者：Liangzhen Cai、Xuanying Qian、Wenjing Song、Taoping Liu、Xiaochun Tao、Wanfang Li、Xiaomin Xie

  DOI：10.1016/j.tet.2014.05.048

  日期：2014.8

  A readily accessible catalytic system, PdCl2(Ph3P)(2)/Ph3P, was developed for the selective arylation of primary anilines with aryl bromides. The strong influence of solvents and bases on the catalytic activity was observed. In refluxing o-xylene, triphenylphosphine shows high efficiency for Pd-catalyzed intermolecular amination reactions. By changing the bases, mono- and diarylation of primary amines could be selectively achieved in high yields. Moreover, the catalytic system showed good toleration for the steric hindrance of anilines. A series of N,N,N',N'-tetraaryl-1,1'-biphenyl-4,4'-diamines, important intermediates of OLED hole transport materials, were synthesized facilely via coupling reactions between 4,4'-diaminobiphenyls and aryl bromides. (C) 2014 Elsevier Ltd. All rights reserved.