(E)-4-methyl-4'-styryl-1,1'-biphenyl | 1346939-26-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-4-methyl-4'-styryl-1,1'-biphenyl
• 英文别名: (E)-4-methyl-4′-styryl-1,1-biphenyl；1-methyl-4-[4-[(E)-2-phenylethenyl]phenyl]benzene
• CAS: 1346939-26-1
• 化学式: C₂₁H₁₈
• 分子量: 270.374
• InChiKey: UAJVNTIQNXSNLA-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  4-(4-甲基苯基)苯甲醛 在 四(三苯基膦)钯 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 (E)-4-methyl-4'-styryl-1,1'-biphenyl
  参考文献：
  名称：

  Pd（0）催化联苯酮/醛的串联一釜反应与相应的二取代芳基烯烃

  摘要：

  通过联苯酮/醛，甲苯磺酰肼和芳基溴化物（或苄基卤化物）的Pd（0）催化交叉偶联反应，开发了二取代的芳基烯烃。这种方法是通过一锅两步反应完成的，该反应涉及通过将甲苯磺酰肼与联苯酮/醛反应，然后在Pd（PPh 3）4和Pd（PPh 3）存在下与芳基溴化物（或苄基卤化物）偶联来制备N-甲苯磺酰基hydr。叔丁醇锂可以中等到良好的产率生产各种二取代的芳基烯烃。

  DOI：

  10.1002/cjoc.201600870

文献信息

• Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes
  作者：Alasdair K. Cooper、Paul M. Burton、David J. Nelson

  DOI：10.1055/s-0039-1690045

  日期：2020.2

  Suzuki–Miyaura reactions catalysed by nickel and palladium is reported, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has effects on cross-coupling reactions that range

  报道了使用竞争实验，鲁棒性筛选和密度泛函理论计算，比较了官能团对镍和钯催化的铃木-宫浦反应性能的影响的详细比较。镍可以与各种官能团相互作用，这在竞争性交叉偶联反应中表现为选择性。这些官能团在外源性添加剂上的存在对交叉偶联反应有影响，其范围从收率的轻微提高到反应完全停止。相比之下，钯与这些官能团的相互作用不足以引起交叉偶联反应的选择性。钯催化的交叉偶联反应的选择性主要由芳基卤化物的电子性质决定。
• Nickel-Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides
  作者：Mamoru Tobisu、Tian Xu、Toshiaki Shimasaki、Naoto Chatani

  DOI：10.1021/ja207759e

  日期：2011.12.7

  Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.