N-(4-methoxyphenyl)-2,6-diethylaniline | 133477-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxyphenyl)-2,6-diethylaniline
• 英文别名: 2,6-diethyl-N-(4-methoxyphenyl)aniline
• CAS: 133477-73-3
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: VBCIGWNIKCAJAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-溴苯甲醚 、 2,6-二乙基苯胺 在 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 22.0h， 生成 N-(4-methoxyphenyl)-2,6-diethylaniline
  参考文献：
  名称：

  Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride

  摘要：

  While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.08.027

文献信息

• Buchwald–Hartwig amination of aryl esters and chlorides catalyzed by the dianisole-decorated Pd–NHC complex
  作者：Di-Zhong Zheng、Hong-Gang Xiong、A-Xiang Song、Hua-Gang Yao、Chang Xu

  DOI：10.1039/d1ob02051j

  日期：——

  A modular and generic method for the Buchwald–Hartwig amination reactions of relatively unreactive aryl esters as acyl electrophiles and aryl chlorides as aryl electrophiles has been developed, leading to the efficient synthesis of amides/amines under air conditions and with low catalyst loadings. The success of this catalytic protocol is mainly attributed to the modification of the Pd–IPr skeleton

  已经开发了一种模块化和通用的方法，用于将相对不活泼的芳基酯作为酰基亲电试剂和芳基氯化物作为芳基亲电试剂进行 Buchwald-Hartwig 胺化反应，从而在空气条件下和低催化剂负载下有效合成酰胺/胺。该催化方案的成功主要归功于 Pd-IPr 骨架的空间位阻和供电子苯甲醚基团的修饰。该方法还具有良好的官能团耐受性和优异的化学选择性。总之，本文提出的结果表明，有可能为不同的亲电试剂开发一种通用的通用方案以进行 Buchwald-Hartwig 胺化反应，避免过多考虑底物依赖性 C-N 键形成的反应条件。
• Palladate Precatalysts for the Formation of C–N and C–C Bonds
  作者：Caroline M. Zinser、Katie G. Warren、Fady Nahra、Abdullah Al-Majid、Assem Barakat、Mohammad Shahidul Islam、Steven P. Nolan、Catherine S. J. Cazin

  DOI：10.1021/acs.organomet.9b00326

  日期：2019.7.22

  A series of imidazolium-based palladate precatalysts has been synthesized and the catalytic activity of these air- and moisture-stable complexes evaluated as a function of the nature of the imidazolium counterion. These precatalysts can be converted under catalytic conditions to Pd-NHC species capable of enabling the Buchwald-Hartwig aryl amination and the alpha-arylation of ketones. Both reactions can be carried out efficiently under very mild operating conditions. The effectiveness of the protocol was tested on functionality-laden substrates.