(E)-butyl 3-(2-bromophenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-butyl 3-(2-bromophenyl)acrylate
• 英文别名: (e)-Butyl 3-(2-bromophenyl)acrylate；butyl (E)-3-(2-bromophenyl)prop-2-enoate
• 化学式: C₁₃H₁₅BrO₂
• 分子量: 283.165
• InChiKey: RCARQGUBMIMGSR-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烯酸丁酯 、 (E)-butyl 3-(2-bromophenyl)acrylate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以80%的产率得到1,2-di(2-n-butylcarbonyl-trans-vinyl)-benzene
  参考文献：
  名称：

  Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base

  摘要：

  An efficient method was developed for the oxidative Heck reaction between arylboronic acids and olefins catalyzed by anionic palladium complexes of the type [CA](x)[PdCl4] (x = 1,2) and [CA](2)[Pd2Cl6] (CA= imidazolium or pyridinium cation). Molecular oxygen was employed as an environmentally benign oxidant to regenerate Pd(II) species during the reaction. The elaborated protocol could be applied to the coupling of different arylboronic acids with both electron-rich and electron-poor olefins. The catalyst system was further employed for the one-pot oxidative Heck reaction followed by the Heck coupling to build conjugated compounds in good yield.Mass spectrometry (ESI-MS) and UV-vis spectroscopy was used to identify palladium-containing complexes in the reactions. A plausible reaction mechanism of the oxidative Heck reaction was proposed. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.07.003
• 作为产物：
  描述：

  丙烯酸丁酯 、 2-溴苯基硼酸 在 [bmpy]2[PdCl₄] 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以90%的产率得到(E)-butyl 3-(2-bromophenyl)acrylate
  参考文献：
  名称：

  Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base

  摘要：

  An efficient method was developed for the oxidative Heck reaction between arylboronic acids and olefins catalyzed by anionic palladium complexes of the type [CA](x)[PdCl4] (x = 1,2) and [CA](2)[Pd2Cl6] (CA= imidazolium or pyridinium cation). Molecular oxygen was employed as an environmentally benign oxidant to regenerate Pd(II) species during the reaction. The elaborated protocol could be applied to the coupling of different arylboronic acids with both electron-rich and electron-poor olefins. The catalyst system was further employed for the one-pot oxidative Heck reaction followed by the Heck coupling to build conjugated compounds in good yield.Mass spectrometry (ESI-MS) and UV-vis spectroscopy was used to identify palladium-containing complexes in the reactions. A plausible reaction mechanism of the oxidative Heck reaction was proposed. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.07.003

文献信息

• Pd-catalyzed ligand-free desulfitative Heck reaction with arenesulfinic acid salts under air
  作者：Sai Hu、Ping Xia、Kai Cheng、Chenze Qi

  DOI：10.1002/aoc.2970

  日期：2013.3

  Palladium‐catalyzed cross‐coupling reactions of various aryl sulfinic acid salts with a wide variety of vinyl substrates have been achieved in good to excellent yields under simple aerobic conditions at 70°C with the assistance of Cu(II) salts. The reaction can be accelerated by the combination of DMSO with THF. The reported Matsuda–Heck type coupling reactions are tolerant to the common functional

  在简单的好氧条件下，借助Cu（II）盐，在70°C的简单好氧条件下，已实现了各种芳基亚磺酸盐与各种乙烯基底物的钯催化交叉偶联反应。DMSO与THF的结合可以加速反应。已报道的Matsuda-Heck型偶联反应可耐受常见的官能团，从而使这些转化成为传统交叉偶联方法的诱人替代品。版权所有©2013 John Wiley＆Sons，Ltd.
• Highly Efficient, Recyclable Pd(II) Catalysts with Bisimidazole Ligands for the Heck Reaction in Ionic Liquids
  作者：Soon Bong Park、Howard Alper

  DOI：10.1021/ol030071d

  日期：2003.9.1

  [reaction: see text] New Pd(II) complexes with bisimidazole ligands were prepared and proved to be effective catalysts for the Heck reaction under phosphine-free conditions using ionic liquids as solvents. This system could be recycled five times without any loss of catalytic activity.

  [反应：见正文]制备了具有联咪唑配体的新型Pd（II）配合物，并证明是使用离子液体作为溶剂在无膦条件下进行Heck反应的有效催化剂。该系统可以循环使用五次，而不会损失任何催化活性。
• Palladiumimmobilized on chitosan nanofibers cross-linked by glutaraldehyde as an efficient catalyst for the Mizoroki–Heck reaction
  作者：Z. Wang、M. Xu、L. Shao、C. Qi

  DOI：10.1134/s0023158416030149

  日期：2016.5

  acetic acid aqueous solution. The CS/PEO fiber mats were treated with glutaraldehyde aqueous solution to stabilize fibers in solution. The concentration of glutaraldehyde is important for incorporating swelling properties in the cross-linked CS/PEO fiber mats. The cross-linked CS/PEO fibers (CCS/PEO fibers) were then used as supports for palladium catalysts in the Mizoroki–Heck reaction. The results

  通过将CS和聚环氧乙烷（PEO）的混合物在乙酸水溶液中进行静电纺丝，成功制备了非织造的壳聚糖（CS）纳米纤维毡。CS / PEO纤维毡用戊二醛水溶液处理以稳定溶液中的纤维。戊二醛的浓度对于在交联的CS / PEO纤维毡中加入溶胀性能很重要。然后将交联的CS / PEO纤维（CCS / PEO纤维）用作Mizoroki-Heck反应中钯催化剂的载体。研究结果表明，负载在CCS / PEO纤维（Pd-CCS / PEO纤维）上的Pd催化剂的催化活性高度依赖于交联过程中戊二醛的浓度。密度泛函理论（DFT）计算表明，CS和戊二醛之间形成的席夫（Schiff）键可以减少在CCS / PEO纤维和钯活性物质之间形成螯合物的所需能量。反过来，这可能会降低在Pd-CCS / PEO纤维催化剂存在下发生的Mizoroki-Heck反应的活化能。优化的Pd-CCS / PEO纤维催化剂在芳族碘化物与烯烃的Mi
• Encapsulating palladium nanoparticles inside ethylenediamine functionalized and crosslinked chlorinated poly(vinyl chloride) nanofibers as an efficient and stable heterogeneous catalyst for coupling reactions
  作者：Min Qin、Qingqing Wang、Yijun Du、Linjun Shao、Chenze Qi、Hongyu Tao

  DOI：10.1016/j.jpcs.2020.109674

  日期：2020.12

  characterizations. The catalytic performance of these palladium encapsulated CPVC nanofibers (Pd@ACPVC) have been evaluated by the Heck and Sonogashira reactions. The catalysis results demonstrate that this Pd@ACPVC catalyst was very effective and stable to catalyze the coupling reaction of aromatic iodides with alkenes (Heck reaction) or phenyl acetylene (Sonogashira reaction) to afford the coupling products in moderate

  摘要 将氯化钯和氯化聚（氯乙烯）（CPVC）混合物制备成均匀溶液，然后通过静电纺丝制备平均直径约 460 nm 的均匀纳米纤维。然后，这些复合纳米纤维在乙二胺溶液中进行处理，使纳米纤维内部的 CPVC 分子功能化和交联，以提高它们的螯合能力和耐溶剂性。SEM、FT-IR、EA 和 PALS 表征证实了复合纳米纤维内 CPVC 分子的功能化和交联。这些钯包封的 CPVC 纳米纤维 (Pd@ACPVC) 的催化性能已通过 Heck 和 Sonogashira 反应进行评估。催化结果表明，该 Pd@ACPVC 催化剂非常有效且稳定地催化芳族碘化物与烯烃（Heck 反应）或苯乙炔（Sonogashira 反应）的偶联反应，以中等至优异的产率提供偶联产物。由于规则的纤维结构，Pd@ACPVC 可以很容易地从反应混合物中分离和回收。此外，Pd@ACPVC 可以分别重复用于 Heck 反应 10 次和 Sonogashira
• 2-Hydroxy-1,10-phenanthroline vs 1,10-Phenanthroline: Significant Ligand Acceleration Effects in the Palladium-Catalyzed Oxidative Heck Reaction of Arenes
  作者：Cheng-Hao Ying、Shao-Bai Yan、Wei-Liang Duan

  DOI：10.1021/ol4033804

  日期：2014.1.17

  A series of bidentate monoanionic nitrogen ligands were designed and applied in the Pd-catalyzed oxidative Heck reaction of arenes with alkenes. Significant ligand-accelerated effects were observed, and direct C-H functionalized products were formed in high yields with meta-selectivity.