4'-ethenyl-2-methylbiphenyl

• 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'-ethenyl-2-methylbiphenyl
• 英文别名: 2-methyl-4'-vinylbiphenyl；4-(2-methylphenyl)-1-vinylbenzene；1-Ethenyl-4-(2-methylphenyl)benzene
• 化学式: C₁₅H₁₄
• 分子量: 194.276
• InChiKey: GXMRYVSTCLCSJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-氯甲苯 、 4-乙烯基苯硼酸 在 carbapalladacycle complex*periodic mesoporous organosilica potassium carbonate 作用下， 反应 24.0h， 以10%的产率得到4'-ethenyl-2-methylbiphenyl
  参考文献：
  名称：

  A periodic mesoporous organosilica containing a carbapalladacycle complex as heterogeneous catalyst for Suzuki cross-coupling

  摘要：

  A series of periodic mesoporous organosilica with varying contents of a carbapalladacycle complex forming part of the walls of the hybrid material has been prepared. These solids have a very large surface area (ca. 1000 m(2) g(-1)), a mononodal pore size distribution (ca. 3 nm), and a periodic hexagonal structure typical for MCM-41 materials. The fresh solids exhibit high activity for the Suzuki cross-coupling of phenylboronic acid with bromobenzoic acid and bromoacetophenone. The initial catalytic activity of these PMO materials is significantly higher than that of a related amorphous silica catalyst containing the same complex. Leaching studies, either filtering the solid in hot solution or three-phase-test attaching one of the reagents to a solid, demonstrate that there is a contribution to the catalysis of leached species from the solid into the solution. The solid can be reused although a progressive deactivation caused by complex degradation, and mesopore collapse has been observed. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2004.11.006

文献信息

• [Pd(Cl)2{P(NC5H10)(C6H11)2}2]-A Highly Effective and Extremely Versatile Palladium-Based Negishi Catalyst that Efficiently and Reliably Operates at Low Catalyst Loadings
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/chem.201001201

  日期：——

  electronically activated, non‐activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100 °C in the presence of just 0.01 mol % of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetals, lactones, amides, anilines,

  [Pd（Cl）2 P（NC 5 H 10）（C 6 H 11）2 } 2 ]（1）已通过使市售的[Pd（cod）（Cl）2 ]反应定量制备。室温下在几分钟内在N 2中与易于制备的1-（二环己基膦酰基）哌啶在甲苯中的环辛二烯）。综合大楼1已被证明是极佳的Negishi催化剂，能够将各种电子活化，非活化，失活，空间受阻，杂环和官能化的芳基溴化物与各种（也是杂环的）芳基锌试剂定量偶联，通常在几分钟内即可完成。 100°C，仅存在0.01 mol％的催化剂。含有硝基，腈，醚，酯，羟基，羰基和羧基的芳基溴化物，以及缩醛，内酯，酰胺，苯胺，烯烃，羧酸，乙酸，吡啶和嘧啶已被成功用作偶联伙伴。此外，在两个反应伙伴中都可以容忍电子和空间变化。实验观察强烈表明分子机制是有效的。
• A rapid and efficient catalysis system for the synthesis of 4-vinylbiphenyl derivatives
  作者：Xiaowei Ma、Yan Liu、Ping Liu、Jianwei Xie、Bin Dai、Zhiyong Liu

  DOI：10.1002/aoc.3045

  日期：2013.12

  A series of 4‐vinylbiphenyl derivatives were synthesized by Pd(OAc)2/PCy3‐catalyzed Suzuki–Miyaura reaction in the presence of K3PO4.3H2O as base in toluene at 80°C for only 10–30 min, and the corresponding products achieved 65–98% yields. According to this efficient C―C bond‐forming method, the obtained yields of 4‐vinylbiphenyl liquid crystal compounds were up to 92–96%. Copyright © 2013 John Wiley

  在甲苯中以K 3 PO 4 .3H 2 O为碱的情况下，在80°C下仅10-30分钟的时间内，通过Pd（OAc）2 / PCy 3催化的Suzuki-Miyaura反应合成了一系列4-乙烯基联苯衍生物。，相应的产品可达到65-98％的收率。根据这种有效的CC键形成方法，获得的4-乙烯基联苯液晶化合物的产率高达92-96％。版权所有©2013 John Wiley＆Sons，Ltd.
• Structure, dynamics and catalytic activity of palladium(II) complexes with imidazole ligands
  作者：M.S. Szulmanowicz、W. Zawartka、A. Gniewek、A.M. Trzeciak

  DOI：10.1016/j.ica.2010.08.037

  日期：2010.12

  Several palladium complexes of the type [Pd(im)(2)Cl-2], [Pd(im)(3)Cl]Cl, and [Pd(im)(4)]Cl-2 (im = imidazole 1,1-methylimidazole 2, 1,2-dimethylimidazole 3, 1-butylimidazole 4, 4a, 1-phenylimidazole 6, 1-phenylimidazoline 7, and 1-methylimidazoline 8) were prepared and structurally characterized. The square planar structure of two new complexes with the composition [Pd(im)(4)]Cl-2 (2b, 4b) was confirmed by X-ray analysis. In solution, exchange of imidazole ligands leading to heteroleptic products was evidenced by ESI-MS studies. Two bis-ligated complexes, bearing 1-methylimidazole (2a) and 1-propoxymethylimidazole (5) ligands, were obtained in the reaction of palladium with imidazoles formed by deprotection of one nitrogen atom in the respective imidazolium halides. Catalytic Suzuki-Miyaura reactions were carried out using the obtained palladium complexes in isopropanol-water solution. High yields of the cross-coupling products were obtained at 40 and 60 degrees C when 2-bromotoluene, 4-bromotoluene, and 4-bromoanizole were used as substrates. (C) 2010 Elsevier B.V. All rights reserved.
• Air-Stable Dinuclear Iodine-Bridged Pd(I) Complex - Catalyst, Precursor, or Parasite? The Additive Decides. Systematic Nucleophile-Activity Study and Application as Precatalyst in Cross-Coupling
  作者：Marialuisa Aufiero、Thomas Scattolin、Fabien Proutière、Franziska Schoenebeck

  DOI：10.1021/acs.organomet.5b00766

  日期：2015.10.26

  Dinuclear Pd(I) complexes were recently shown to potentially adopt various possible roles in catalysis, being capable of functioning as catalyst via dinuclear catalysis cycles, precatalyst for Pd(0), or inhibitor. This report examines the factors that control the mechanistic role in catalysis. Our data suggest that the transformation to Pd(0) occurs via nudeophile-induced fragmentation of Pd(I) Pd(I). A systematic study examining the nudeophilicity of additive versus activity was undertaken that revealed the minimum nudeophilicity necessary to activate two structurally very similar Pd(I) dimers, [Pd(mu-X) (PtBu3)](2) (X = I or Br). While the more labile bromine-bridged Pd(I) dirner is converted to Pd(0) with nudeophiles N >= 10.5, the iodine-bridged analogue requires N >= 16.1 (N according to Mayr's scale). Too strong nudeophiles generate a high concentration of unstable monoligated Pd(0) rapidly, leading to Pd loss (i.e., Pd black). On the other hand, careful tuning of nudeophilicity allows for a controlled release of well-defined Pd(0) species. These insights have led to the first application of the air-stable and previously thought unreactive iodine-bridged dimer [Pd(mu-I) (PtBu3)](2) as a precatalyst for monoligated Pd(0) in cross-coupling reactions. The reactions were performed without exclusion of oxygen-all reagents were handled in air without special precautions. Highly efficient Kumada couplings of aryl iodides and bromides were achieved in <5 min at room temperature.
• A periodic mesoporous organosilica containing a carbapalladacycle complex as heterogeneous catalyst for Suzuki cross-coupling
  作者：Avelino Corma、Debashis Das、Hermenegildo García、Antonio Leyva

  DOI：10.1016/j.jcat.2004.11.006

  日期：2005.1

  A series of periodic mesoporous organosilica with varying contents of a carbapalladacycle complex forming part of the walls of the hybrid material has been prepared. These solids have a very large surface area (ca. 1000 m(2) g(-1)), a mononodal pore size distribution (ca. 3 nm), and a periodic hexagonal structure typical for MCM-41 materials. The fresh solids exhibit high activity for the Suzuki cross-coupling of phenylboronic acid with bromobenzoic acid and bromoacetophenone. The initial catalytic activity of these PMO materials is significantly higher than that of a related amorphous silica catalyst containing the same complex. Leaching studies, either filtering the solid in hot solution or three-phase-test attaching one of the reagents to a solid, demonstrate that there is a contribution to the catalysis of leached species from the solid into the solution. The solid can be reused although a progressive deactivation caused by complex degradation, and mesopore collapse has been observed. (C) 2004 Elsevier Inc. All rights reserved.