2,3,5,6-tertrafluoro-4’-methoxy-4-methyl-1,1’-biphenyl | 1206164-35-3

• 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: 2,3,5,6-tertrafluoro-4’-methoxy-4-methyl-1,1’-biphenyl
• 英文别名: 2,3,5,6-tetrafluoro-4'-methoxy-4-methylbiphenyl；2,3,5,6-tetrafluoro-4'-methoxy-4-methyl-1,1'-biphenyl；2,3,5,6-Tetrafluoro-4'-methoxy-4-methylbiphenyl；1,2,4,5-tetrafluoro-3-(4-methoxyphenyl)-6-methylbenzene
• CAS: 1206164-35-3
• 化学式: C₁₄H₁₀F₄O
• 分子量: 270.226
• InChiKey: VQEYQJPUASDNJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-碘苯甲醚 、 potassium 4-methyl tetrafluorobenzoate 在 copper(l) iodide 、 1,10-菲罗啉 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以97%的产率得到2,3,5,6-tertrafluoro-4’-methoxy-4-methyl-1,1’-biphenyl
  参考文献：
  名称：

  多氟苯甲酸钾与芳基碘化物和溴化物的铜催化脱羧交叉偶联

  摘要：

  仅适用于铜：使用铜催化剂，易于获得且不挥发的多氟苯甲酸钾与芳基碘化物和溴化物的脱羧交叉偶联可提供极佳的收率的多氟联芳基和多氟苯磺酸酯（请参见方案）。报告了标题反应的机理分析。

  DOI：

  10.1002/anie.200904916

文献信息

• Pd-Catalyzed Decarboxylative Cross Coupling of Potassium Polyfluorobenzoates with Aryl Bromides, Chlorides, and Triflates
  作者：Rui Shang、Qing Xu、Yuan-Ye Jiang、Yan Wang、Lei Liu

  DOI：10.1021/ol100008q

  日期：2010.3.5

  Pd-catalyzed decarboxylative cross coupling of potassium polyfluorobenzoates with aryl bromides, chlorides, and triflates is achieved by using diglyme as the solvent. The reaction is useful for synthesis of polyfluorobiaryls from readily accessible and nonvolatile polyfluorobenzoate salts. Unlike the Cu-catalyzed decarboxylation cross coupling where oxidative addition is the rate-limiting step, in

  通过使用二甘醇二甲醚作为溶剂可实现多氟苯甲酸钾与芳基溴化物，氯化物和三氟甲磺酸酯的钯催化脱羧交叉偶联。该反应可用于由容易获得的非挥发性多氟苯甲酸盐合成多氟联芳基。与其中氧化加成是限速步骤的Cu催化的脱羧交叉偶联不同，在Pd催化的形式中，脱羧是限速步骤。
• Highly efficient heterogeneous copper-catalyzed decarboxylative cross-coupling of potassium polyfluorobenzoates with aryl halides leading to polyfluorobiaryls
  作者：Yang Lin、Mingzhong Cai、Zhiqiang Fang、Hong Zhao

  DOI：10.1039/c7ra05711c

  日期：——

  reaction of potassium polyfluorobenzoates with aryl iodides and bromides was achieved in diglyme or DMAc at 130 or 160 °C in the presence of 10–20 mol% of a 1,10-phenanthroline-functionalized MCM-41-immobilized copper(I) complex, [MCM-41-Phen-CuI], yielding a variety of polyfluorobiaryls in good to excellent yields. This heterogeneous copper(I) complex could easily be prepared via a simple procedure

  多氟苯甲酸钾与芳基碘化物和溴化物的异质脱羧交叉偶联反应是在130或160°C的二甘醇二甲醚或DMAc中，在10–20 mol％的1,10-菲咯啉官能化的MCM-41固定化的情况下完成的铜（I）配合物[MCM-41-Phen-CuI]，可产生多种多氟联芳基化合物，收率好至极好。这种异质的铜（I）络合物可以通过简单的方法轻松地从市售易得的廉价试剂中制备，具有与均相CuI / Phen系统相同的催化活性，并且可以通过过滤反应溶液进行回收并循环至少8次。倍，而没有明显丧失催化活性。
• Nickel-Catalyzed Decarboxylative Cross-Coupling of Perfluorobenzoates with Aryl Halides and Sulfonates
  作者：Logan W. Sardzinski、William C. Wertjes、Abigail M. Schnaith、Dipannita Kalyani

  DOI：10.1021/acs.orglett.5b00241

  日期：2015.3.6

  for the coupling of perfluorobenzoates with aryl halides and pseudohalides is described. Aryl iodides, bromides, chlorides, triflates, and tosylates participate in these transformations to afford the products in good yields. Penta-, tetra-, and trifluorinated biaryl compounds are obtained using these newly developed Ni-catalyzed decarboxylative cross-coupling reactions.

  描述了一种Ni-催化的方法，用于将全氟苯甲酸酯与芳基卤化物和拟卤化物偶合。芳基碘化物，溴化物，氯化物，三氟甲磺酸盐和甲苯磺酸盐参与这些转化过程，从而以高收率获得产物。使用这些新开发的Ni催化的脱羧交叉偶联反应可得到五氟，四氟和三氟联芳基化合物。
• Palladium-Catalyzed Direct Arylation of Polyfluoroarenes with Organosilicon Reagents
  作者：Huixin Fan、Yaping Shang、Weiping Su

  DOI：10.1002/ejoc.201402091

  日期：2014.6

  The palladium-catalyzed direct arylation of polyfluoroarenes with organosilicon reagents was achieved by establishing general reaction conditions. This protocol was compatible with a broad range of functional groups and offered the desired products in moderate to good yields.

  通过建立一般反应条件，实现了钯催化的多氟芳烃与有机硅试剂的直接芳基化反应。该协议与广泛的官能团兼容，并以中等至良好的产量提供所需的产品。
• Pd-Catalyzed Direct Arylation of Polyfluoroarenes on Water under Mild Conditions Using PPh₃ Ligand
  作者：Fei Chen、Qiao-Qiao Min、Xingang Zhang

  DOI：10.1021/jo300036d

  日期：2012.3.16

  We report a Pd-catalyzed direct arylation of polyfluoroarenes with aryl iodides. The advantages of this reaction are its high reaction efficiency, excellent functional group compatibility, mild reaction conditions (70 degrees C), inexpensive PPh3 ligand, and use of pure water as reaction medium. The usefulness of this reaction has also been demonstrated by rapid preparation of highly functionalized polyfluoroarenes via iterative Pd-catalyzed C-H bond functionalization.