N-(3,5-dimethylphenyl)-N-ethylaniline

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3,5-dimethylphenyl)-N-ethylaniline
• 英文别名: N-ethyl-N-(3,5-dimethylphenyl)aniline；N-(3,5-xylyl)-N-ethylaniline；N-ethyl-3,5-dimethyl-N-phenylaniline
• 化学式: C₁₆H₁₉N
• 分子量: 225.334
• InChiKey: XRTVZFPLLNCVHP-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,3-二甲基-5-碘苯 、 N-乙基苯胺 在 tris(dibenzylideneacetone)dipalladium (0) 、 sodium t-butanolate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到N-(3,5-dimethylphenyl)-N-ethylaniline
  参考文献：
  名称：

  An Improved Method for the Palladium-Catalyzed Amination of Aryl Iodides

  摘要：

  Aryl iodides are coupled with amines to give the corresponding arylamines in high yield in the presence of palladium, a suitable ligand, and NaOt-Bu. Functionalized aryl iodides give good yields of the corresponding arylamines when Cs2CO3 is substituted as the base.

  DOI：

  10.1021/jo0008486

文献信息

• The use of palladium chloride as a precatalyst for the amination of aryl bromides
  作者：Xiao-Xiang Zhang、Michele C Harris、Joseph P Sadighi、Stephen L Buchwald

  DOI：10.1139/v01-152

  日期：2001.11.1

  The use of palladium chloride as a precatalyst for the amination of aryl bromides is reported. To overcome the poor solubility of palladium chloride in commonly used solvents, a procedure was developed in which PdCl₂ was preheated with neat amine in the presence of a phosphine ligand before the addition of the other reaction components. This protocol is effective for a broad range of substrate combinations using several types of phosphine ligands.Key words: palladium chloride, amination, aryl bromide, phosphine ligand.

  报道了氯化钯作为芳基溴化物氨基化的预催化剂的使用。为了克服氯化钯在常用溶剂中溶解度较低的问题，开发了一种方法，即在添加其他反应组分之前，在膦配体的存在下，将PdCl₂与纯胺预热。该方案对于使用几种类型的膦配体的广泛底物组合是有效的。关键词：氯化钯，氨基化，芳基溴化物，膦配体。
• Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates
  作者：John P. Wolfe、Hiroshi Tomori、Joseph P. Sadighi、Jingjun Yin、Stephen L. Buchwald

  DOI：10.1021/jo991699y

  日期：2000.2.1

  Palladium complexes supported by (o-biphenyl)P(t-Bu)(2) (3) or (o-biphenyl)PCy2 (4) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand 3 allows for the room-temperature catalytic amination of many aryl chloride, bromide, and triflate substrates, while ligand 4 is effective for the amination of functionalized substrates or reactions of acyclic secondary amines. The catalysts perform well for a large number of different substrate combinations at 80-110 degrees C, including chloropyridines and functionalized aryl halides and triflates using 0.5-1.0 mol % Pd; some reactions proceed efficiently at low catalyst levels (0.05 mol % Pd). These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date. Ligands 3 and 4 are air-stable, crystalline solids that are commercially available. Their effectiveness is believed to be due to a combination of steric and electronic properties that promote oxidative addition, Pd-N bond formation, and reductive elimination.
• Palladium-Catalyzed Amination of Aryl Bromides:  Use of Phosphinoether Ligands for the Efficient Coupling of Acyclic Secondary Amines
  作者：Jean-François Marcoux、Seble Wagaw、Stephen L. Buchwald

  DOI：10.1021/jo9622946

  日期：1997.3.1
• LIGANDS FOR METALS AND METAL-CATALYZED PROCESSES
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP1097158B1

  公开（公告）日：2006-01-25
• Ligands for metals and improved metal-catalyzed processes based thereon
  申请人：Massachussetts Institute of Technology

  公开号：EP1354887B1

  公开（公告）日：2007-04-25