4'-(tert-butyl)-2,6-dimethyl-1,1'-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: 4'-(tert-butyl)-2,6-dimethyl-1,1'-biphenyl
• 英文别名: 2,6-dimethyl-4'-tert-butylbiphenyl；4'-tert-butyl-2,6-dimethylbiphenyl；2-(4-Tert-butylphenyl)-1,3-dimethylbenzene
• 化学式: C₁₈H₂₂
• 分子量: 238.373
• InChiKey: JRHATMRTHCJWTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-氯-1,3-二甲苯 、 4-叔丁基苯硼酸 在 C₄₃H₄₆ClF₆N₃Pd 、 potassium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.0h， 以94%的产率得到4'-(tert-butyl)-2,6-dimethyl-1,1'-biphenyl
  参考文献：
  名称：

  支持配体辅助的N-杂环卡宾钯配合物：在芳烃和杂芳族氯化物与各种硼酸之间的Suzuki-Miyaura交叉偶联中表征，计算和催化活性

  摘要：

  已开发出一系列新的亚胺-Pd- （N-杂环卡宾）配合物，作为Pd催化的Suzuki-Miyaura偶联反应的有效催化剂。基于支持配体的性能，已通过实验和计算模型证明了结构与催化活性之间的相关性。芳基和杂芳族氯化物的广泛反应范围可以在极低的催化剂负载量（最低0.005 mol％）下进行。

  DOI：

  10.1016/j.tetlet.2016.03.086

文献信息

• Highly Active Palladium Catalysts for Suzuki Coupling Reactions
  作者：John P. Wolfe、Robert A. Singer、Bryant H. Yang、Stephen L. Buchwald

  DOI：10.1021/ja992130h

  日期：1999.10.1

  room-temperature Suzuki coupling of aryl bromides and aryl chlorides with 0.5−1.0 mol % Pd. Use of o-(dicyclohexylphosphino)biphenyl (2) allows Suzuki couplings to be carried out at low catalyst loadings (0.000001−0.02 mol % Pd). The process tolerates a broad range of functional groups and substrate combinations including the use of sterically hindered substrates. This is the most active catalyst system in

  乙酸钯和邻（二叔丁基膦）联苯 (4) 的混合物催化芳基溴和芳基氯与 0.5-1.0 mol% Pd 的室温 Suzuki 偶联。使用邻（二环己基膦基）联苯 (2) 允许在低催化剂负载（0.000001-0.02 mol% Pd）下进行 Suzuki 偶联。该工艺可以容忍广泛的官能团和底物组合，包括使用空间位阻底物。这是迄今为止已报道的在反应温度、转换数和空间耐受性方面最活跃的催化剂体系。
• Palladacycles derived from arylphosphinamides for mild Suzuki–Miyaura cross-couplings
  作者：Guo-Jie Wu、Fu-She Han、Yu-Long Zhao

  DOI：10.1039/c5ra12742d

  日期：——

  of palladacycles, a wide variety of aryl bromides and boronic acids could be coupled very efficiently at ambient temperature and under air atmosphere without the need of external supporting ligands. Moreover, the mild conditions also allow for smooth coupling of electron-deficient, i.e., the less stable aryl triflates. In addition to the highly catalytic activity, the palladacyclic complexes can be

  我们介绍了一种衍生自芳基次膦酰胺的Palladacyclic配合物，可用作轻度的Suzuki-Miyaura交叉偶联的有效和通用的预催化剂。在存在1.0mol％的Palladacycles的情况下，可以在环境温度和空气气氛下非常有效地偶联各种各样的芳基溴化物和硼酸，而无需外部支持配体。此外，温和的条件还可以使电子不足的平滑耦合，即，不稳定的芳基三氟甲磺酸酯。除具有高催化活性外，还可以通过两步法很容易地从容易负担得起的二苯基次膦酰氯中制备四环化合物，并且对空气和湿气显示出极好的稳定性。由于这些突出的特性，新的palladacycles将在Suzuki-Miyaura联轴器中找到实际应用。
• A General Palladium Catalyst System for Suzuki−Miyaura Coupling of Potassium Aryltrifluoroborates and Aryl Mesylates
  作者：Wing Kin Chow、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1021/jo100846t

  日期：2010.8.6

  The first general examples of palladium-catalyzed Suzuki-type cross-coupling of aryl and heteroaryl mesylates with potassium aryl and heteroaryltrifluoroborates are presented. In addition to biaryl couplings, the cross-coupling reactions of aryl mesylates with alkyl and vinyltrifluoroborate salts have also been successfully accomplished.

  给出了芳基和杂芳基甲磺酸酯与芳基钾和杂芳基三氟硼酸钾的钯催化的Suzuki型交叉偶联的第一个一般实例。除了联芳基偶合以外，还成功地完成了甲磺酸甲基芳基酯与烷基和乙烯基三氟硼酸酯盐的交叉偶联反应。
• Efficient Catalyst for the Suzuki−Miyaura Coupling of Potassium Aryl Trifluoroborates with Aryl Chlorides
  作者：Timothy E. Barder、Stephen L. Buchwald

  DOI：10.1021/ol0491686

  日期：2004.8.1

  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl- and heteroaryl chlorides with potassium aryl- and heteroaryltrifluoroborates have been accomplished with the supporting ligand S-Phos in good to excellent yield. Hindered biaryls and substrates containing a variety of functional groups can be prepared. Suzuki-Miyaura couplings of a 3-pyridyl boron-based nucleophile with aryl- and

  芳基氯和杂芳基氯化物与芳基三氟硼酸钾和杂芳基三氟硼酸钾的钯催化Suzuki-Miyaura交叉偶联反应已经很好地实现了配体S-Phos。可以制备受阻的联芳基和含有多种官能团的底物。基于3-吡啶基硼的亲核试剂与芳基氯化物和杂芳基氯化物的Suzuki-Miyaura偶联以良好或非常好的收率进行。[反应：看文字]
• Novel monoligated imine–Pd–NHC complexes: extremely active pre-catalysts for Suzuki–Miyaura coupling of aryl chlorides
  作者：An Shen、Chen Ni、Yu-Cai Cao、Hui Zhou、Gong-Hua Song、Xiao-Feng Ye

  DOI：10.1016/j.tetlet.2014.04.044

  日期：2014.5

  Novel monoligated imine-Pd-NHC pre-catalysts with extremely high activity for the coupling of aryl chlorides and aryl boronic acids have been well explored. Three diffident catalysts could be obtained through one reaction. Changes in imine ligands would lead to remarkable variation on catalytic activity. Under mild reaction conditions, high reaction yields were achieved. A wide range of biphenyls could be efficiently obtained at ultra low catalyst loadings of 0.005 mol %. (C) 2014 Elsevier Ltd. All rights reserved.