ethyl 2', 3', 4', 5', 6'-pentafluorobiphenyl-4-carboxylate

• 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: ethyl 2', 3', 4', 5', 6'-pentafluorobiphenyl-4-carboxylate
• 英文别名: ethyl 2,3,4,5,6-pentafluoro-1,1'-biphenyl-4-carboxylate；ethyl 2',3',4',5',6'-pentafluorobiphenyl-4-carboxylate；2,3,4,5,6-pentafluoro-4'-ethoxycarbonylbiphenyl；2,3,4,5,6-pentafluoro-4'-carbethoxybiphenyl；ethyl (4-pentafluorophenyl)benzoate；ethyl 4-(2,3,4,5,6-pentafluorophenyl)benzoate
• 化学式: C₁₅H₉F₅O₂
• 分子量: 316.227
• InChiKey: QDWWGWXTLHUMJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-溴苯甲酸乙酯 、 五氟苯 在 sodium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以58%的产率得到ethyl 2', 3', 4', 5', 6'-pentafluorobiphenyl-4-carboxylate
  参考文献：
  名称：

  Palladium nanocrystals stabilized by cucurbit[6]uril as efficient heterogeneous catalyst for direct C–H functionalization of polyfluoroarenes

  摘要：

  Palladium nanocrystals (Pd NCs) featuring abundant surface defects are successfully synthesized by using cucurbit[6]uril as a stabilizer. Employing the as-prepared Pd NCs as catalyst, an efficient approach to the direct C-H functionalization of electron-deficient polyfluoroarenes has been developed. The stable Pd NCs catalyst exhibits excellent catalytic activity and good recyclability with significantly low catalyst loading. The catalytic procedure is insensitive to air and moisture and can be manipulated under ambient environment with operational ease. Mechanistic experiments have provided credible data to support a heterogeneous catalytic mechanism of the present system. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2014.10.013

文献信息

• Copper-Catalyzed Decarboxylative Cross-Coupling of Potassium Polyfluorobenzoates with Aryl Iodides and Bromides
  作者：Rui Shang、Yao Fu、Yan Wang、Qing Xu、Hai-Zhu Yu、Lei Liu

  DOI：10.1002/anie.200904916

  日期：2009.11.23

  For copper only: The decarboxylative cross‐coupling of readily accessible and nonvolatile potassium polyfluorobenzoates with aryl iodides and bromides using a copper catalyst provides polyfluorobiaryls and polyfluorostilbenes in excellent yields (see scheme). Mechanistic analyses are reported for the title reaction.

  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。
• The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH2Hal (Hal=Br, Cl)
  作者：Anton Yu. Shabalin、Nicolay Yu. Adonin、Vadim V. Bardin、Valentin N. Parmon

  DOI：10.1016/j.tet.2014.04.019

  日期：2014.6

  the nature of bulky phosphines used as ligands. As a result, conditions for involving the electron-deficient organoboron reagent—potassium pentafluorophenyltrifluoroborate—in the palladium-catalyzed cross-coupling with aryl bromides and aryl chlorides were identified. It was demonstrated that the chosen conditions are appropriate for the reaction of K[C6F5BF3] with benzyl chloride and benzyl bromide

  研究了配体性质对钯催化剂催化弱亲核性五氟苯基三氟硼酸钾与偶合芳族卤化物ArHal（Hal = Br，Cl）的行为的模仿，该反应亲和力弱的亲核五氟苯基三氟硼酸钾的行为。发现由Pd（OAc）2和合适的含磷配体原位产生的催化剂的活性和反应选择性取决于用作配体的大膦的性质。结果，确定了在钯催化的与芳基溴化物和芳基氯化物的交叉偶联中涉及缺电子的有机硼试剂（五氟苯基三氟硼酸钾）的条件。结果表明，所选择的条件适合于K [C 6F 5 BF 3 ]与苄基氯和苄基溴衍生的五氟苯基芳基甲烷，C 6 F 5 CH 2 Ar。
• 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。
• 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 Coupling Reaction of Perfluoroarenes with Diarylzinc Compounds
  作者：Masato Ohashi、Ryohei Doi、Sensuke Ogoshi

  DOI：10.1002/chem.201303451

  日期：2014.2.10

  to promote the oxidative addition of one CF bond of C6F6 to palladium. Stoichiometric reactions revealed that an expected oxidative‐addition product, trans‐[Pd(C6F5)I(PCy3)2], generated from the reaction of [Pd(PCy3)2] with C6F6 in the presence of lithium iodide, was not involved in the catalytic cycle. Instead, a transient three‐coordinate, monophosphine‐ligated species, [Pd(C6F5)I(PCy3)], emerged

  该报告描述了六氟苯（C 6 F 6）与二芳基锌化合物的首次Pd 0催化交叉偶联，得到了多种五氟苯基芳烃。该反应可以应用于其他全氟芳烃，例如八氟甲苯，五氟吡啶和全氟萘，以得到相应的多氟偶联产物。在该催化反应中的最佳配体是PCy 3，碘化锂作为偶联反应的添加剂是必不可少的。碘化锂在该催化反应中的作用之一是促进C 6 F 6的一个CF键的氧化加成。钯。化学计量反应表明，在存在条件下，[Pd（PCy 3）2 ]与C 6 F 6的反应产生了预期的氧化加成产物反式[Pd（C 6 F 5）I（PCy 3）2 ]。碘化锂的一部分不参与催化循环。取而代之的是，瞬态三配位单膦连接的物质[Pd（C 6 F 5）I（PCy 3）]出现为催化循环中的潜在中间体。因此，我们分离了一种新型的Pd II复合物[Pd（C 6 F 5）I（PCy3）（py）]，其中吡啶（py）充当不稳定的配体以生成瞬态物质。实际上，在碘化锂的存在下，发现该Pd