3-phenyl-2,4,6-trifluorobiphenyl | 1178578-09-0

• 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: 3-phenyl-2,4,6-trifluorobiphenyl
• 英文别名: 1,3,5-Trifluoro-2,4-diphenylbenzene
• CAS: 1178578-09-0
• 化学式: C₁₈H₁₁F₃
• 分子量: 284.281
• InChiKey: OLNZWLFXEAGHKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  328.5±37.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3,5-三氟苯 、 苯 在 copper diacetate 、 palladium diacetate 、 sodium carbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以15%的产率得到2,4,6-trifluorobiphenyl
  参考文献：
  名称：

  Pd(OAc)₂-Catalyzed Oxidative C−H/C−H Cross-Coupling of Electron-Deficient Polyfluoroarenes with Simple Arenes

  摘要：

  Pd(OAc)(2)-catalyzed intermolecular C-H/C-H cross-coupling reactions between electron-deficient polyfluoroarenes and simple arenes for the synthesis of fluorinated biaryls have been developed. Deuterium-labeling experiments suggested that C-H bond cleavage of the simple arenes rather than the polyfluoroarenes is involved in the rate-limiting step.

  DOI：

  10.1021/ja109383e

文献信息

• Copper‐Catalysed Suzuki‐Miyaura Cross‐Coupling of Highly Fluorinated Aryl Boronate Esters with Aryl Iodides and Bromides and Fluoroarene−Arene π‐Stacking Interactions in the Products
  作者：Yudha P. Budiman、Alexandra Friedrich、Udo Radius、Todd B. Marder

  DOI：10.1002/cctc.201901220

  日期：2019.11.7

  combination of copper iodide and phenanthroline as the ligand is an efficient catalyst for Suzuki‐Miyaura cross‐coupling of highly fluorinated boronate esters (aryl−Bpin) with aryl iodides and bromides to generate fluorinated biaryls in good to excellent yields. This method represents a nice alternative to traditional cross‐coupling methods which require palladium catalysts and stoichiometric amounts of

  碘化铜和菲咯啉的配位体组合是高效氟化硼酸酯（芳基-Bpin）与芳基碘化物和溴化物的Suzuki-Miyaura交叉偶联的有效催化剂，可产生高至优收率的氟化联芳基。该方法是传统交叉偶联方法的理想选择，传统交叉偶联方法需要钯催化剂和化学计量的氧化银。我们注意到，在本文研究的部分氟化联芳基晶体中，π⋅⋅⋅π堆叠相互作用主导着分子堆积。它们分别存在于芳烃和全氟芳烃之间，或仅存在于芳烃或全氟芳烃之间。
• Palladium-Catalyzed Direct Arylation of Electron-Deficient Polyfluoroarenes with Arylboronic Acids
  作者：Ye Wei、Jian Kan、Min Wang、Weiping Su、Maochun Hong

  DOI：10.1021/ol901200g

  日期：2009.8.6

  The palladium-catalyzed direct arylation of electron-deficient arenes that contain two or more fluorine groups with arylboronic acids was realized. The key to achieving a broad substrate scope with respect to both polyfluorobenzenes and arylboronic acids is the choice of bases depending on acidities of polyfluorobenzenes.

  实现了钯催化的含两个或多个氟基团的缺电子芳烃与芳基硼酸的直接芳基化。就多氟苯和芳基硼酸而言，获得广泛的底物范围的关键是根据多氟苯的酸度选择碱。
• <i>t</i>Bu₃P-Coordinated 2-Phenylaniline-Based Palladacycle Complexes as Precatalyst for Pd-Catalyzed Coupling Reactions of Aryl Halides with Polyfluoroarenes by a C-H Activation Strategy
  作者：Hong-Hai Zhang、Jie Dong、Qiao-Sheng Hu

  DOI：10.1002/ejoc.201301272

  日期：2014.2

  tBu3P-Coordinated 2-phenylaniline-based palladacycle complex was demonstrated to be an efficient precatalyst for Pd-catalyzed coupling reactions of aryl halides with polyfluoroarenes via C-H activation strategy. The readily accessibility and easy handling nature of tBu3P- coordinated 2-aminobiphenyl-based palladacycle complex and the high yields of the reaction makes tBu3P-coordinated 2-aminobiphenyl-based

  tBu3P配位的基于2-苯基苯胺的palladacycle配合物被证明是通过CH活化策略进行Pd催化的芳基卤化物与多氟芳烃偶联反应的有效预催化剂。tBu3P配位的2-氨基联苯基palladacycle配合物的易接近性和易于处理的性质以及高产率的反应使tBu3P配位的2-氨基联苯基palladacycle配合物成为芳基卤化物与多氟芳烃交叉偶联反应的有吸引力的预催化剂。 。
• Palladium-Catalyzed Cross-Coupling of Polyfluoroarenes with Simple Arenes
  作者：Hu Li、Jia Liu、Chang-Liang Sun、Bi-Jie Li、Zhang-Jie Shi

  DOI：10.1021/ol102688e

  日期：2011.1.21

  The most efficient method to construct biaryls is the direct dehydrogenative cross-coupling of two different aromatic rings. Such an ideal cross arylation starting from distinct polyfluoroarenes and simple arenes was presented. The selectivity of the cross-coupling was controlled by both of the electronic property of fluoroarenes and steric hindrance of simple arenes. Diisopropyl sulfide was essential to promote the efficacy.