ethyl 2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-3-carboxylate | 1361405-07-3

• 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: ethyl 2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-3-carboxylate
• 英文别名: Ethyl 3-(2,3,4,5,6-pentafluorophenyl)benzoate
• CAS: 1361405-07-3
• 化学式: C₁₅H₉F₅O₂
• 分子量: 316.227
• InChiKey: ZHGIZMFFHQLJOE-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：

  五氟苯 、 3-乙氧羰基苯基三氟硼酸钾 在 palladium diacetate 、 silver(l) oxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 15.0h， 以87%的产率得到ethyl 2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-3-carboxylate
  参考文献：
  名称：

  Preparation of fluorinated biaryls through direct palladium-catalyzed coupling of polyfluoroarenes with aryltrifluoroborates

  摘要：

  The direct palladium-catalyzed coupling of polyfluoroarenes with aryltrifluoroborates gave the desired products of fluorinated biaryls in good to excellent yields. A diverse set of important functional groups including methoxy, aldehyde, ester, nitro and halide can be well tolerated in the protocol. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.03.017

文献信息

• Assessing the Cooperating Ability of 6‐Hydroxypicolinic Acid and Pyridyl‐Amide Ligands in Palladium‐Mediated C–H Activation
  作者：Cintya Pinilla、Ana Carmen Albéniz

  DOI：10.1002/ejic.202400076

  日期：——

  and pyridyl amides to act as cooperating ligands in the C−H activation of arenes has been tested by independent experiments. Isolated complexes [Pd(κ2-ligand)(C6F5)py]x− (x=1, 0; ligand=6-oxidopicolinate, pyridyl-amide) were decomposed in arenes leading to the C−H activation of the latter and C6F5-arene coupling products in different amounts which allows to rank the ability of both ligands.

  6-羟基吡啶甲酸和吡啶酰胺在芳烃的 C−H 活化中作为协同配体的能力已通过独立实验进行了测试。分离的复合物 [Pd(κ 2 -配体)(C 6 F 5 )py] x− (x=1, 0;配体=6-氧化吡啶甲酸酯，吡啶基酰胺）在芳烃中分解，导致后者的 C−H 活化和不同量的 C 6 F 5 -芳烃偶联产物，这使得对两个配体的能力进行排名。
• 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.
• Preparation of fluorinated biaryls through direct palladium-catalyzed coupling of polyfluoroarenes with aryltrifluoroborates
  作者：Xin Fang、Yuanyuan Huang、Xiaoqing Chen、Xiaoxi Lin、Zhengshuai Bai、Kuo-Wei Huang、Yaofeng Yuan、Zhiqiang Weng

  DOI：10.1016/j.jfluchem.2013.03.017

  日期：2013.7

  The direct palladium-catalyzed coupling of polyfluoroarenes with aryltrifluoroborates gave the desired products of fluorinated biaryls in good to excellent yields. A diverse set of important functional groups including methoxy, aldehyde, ester, nitro and halide can be well tolerated in the protocol. (c) 2013 Elsevier B.V. All rights reserved.