2-methoxy-2'-(trifluoromethyl)biphenyl | 122801-58-5

• 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-methoxy-2'-(trifluoromethyl)biphenyl
• 英文别名: 2-methoxy-2'-(trifluoromethyl)-1,1'-biphenyl；2-methoxyl-2'-(trifluoromethyl)biphenyl；1-Methoxy-2-[2-(trifluoromethyl)phenyl]benzene
• CAS: 122801-58-5
• 化学式: C₁₄H₁₁F₃O
• 分子量: 252.236
• InChiKey: ZLTSXZUOIGKQLC-UHFFFAOYSA-N

物化性质

• 沸点：
  284.6±40.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 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：
  4

反应信息

• 作为产物：
  描述：

  邻溴三氟甲苯 、 2-甲氧基苯基硼酸 在 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 生成 2-methoxy-2'-(trifluoromethyl)biphenyl
  参考文献：
  名称：

  A mild robust generic protocol for the Suzuki reaction using an air stable catalyst

  摘要：

  A mild but robust procedure has been developed as a first pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable palladium pre-catalyst at low loading (<= 1 mol %) in aqueous solvent mixtures at moderate temperature using potassium carbonate as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding aryl boronic acids to give complete conversion to the product biphenyls in less than 1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature. A further advantage of these mild conditions of moderate temperature, weak base and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. The discovery and fine-tuning of this generic protocol will be presented, supported extensively by examples to illustrate its scope and utility. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.030

文献信息

• General and highly efficient fluorinated-N-heterocyclic carbene–based catalysts for the palladium-catalyzed Suzuki–Miyaura reaction
  作者：Taoping Liu、Xiaoming Zhao、Qilong Shen、Long Lu

  DOI：10.1016/j.tet.2012.05.068

  日期：2012.8

  acid with aryl halides and heteroaryl halides, but also efficient for coupling of other heteroaryl halides and heteroaryl boronic acids. Finally, the catalyst is highly effective for Suzuki–Miyaura reaction of aryl bromides and chlorides with 0.01–0.1 mol % loading if the temperature was raised at refluxed THF/H2O.

  据报道，一种通用且高效的三氟甲基化-N-杂环卡宾（NHC）基催化剂可用于钯催化的Suzuki-Miyaura反应。在催化剂的存在下，未活化的芳基氯和三氟甲磺酸与芳基硼酸的反应在室温下发生，收率好至极好（63-98％）。此外，由Pd（OAc）2 /咪唑鎓盐6a的组合产生的催化剂不仅对于杂芳基硼酸与芳基卤化物和杂芳基卤化物的偶联有效，而且对其他杂芳基卤化物和杂芳基硼酸的偶联有效。最后，如果温度在回流的THF / H 2 O上升高，则该催化剂对于0.01-0.1 mol％负载量的芳基溴化物和氯化物的Suzuki-Miyaura反应非常有效。
• Mild and General Conditions for Negishi Cross-Coupling Enabled by the Use of Palladacycle Precatalysts
  作者：Yang Yang、Nathan J. Oldenhuis、Stephen L. Buchwald

  DOI：10.1002/anie.201207750

  日期：2013.1.7

  A wide range of biaryls were synthesized by palladium‐catalyzed Negishi cross‐couplings at ambient temperature or with low catalyst loading. This protocol features the use of a recently reported aminobiphenyl palladacycle precatalyst to generate the catalytically active XPhosPd0 species. Significantly, a wide range of challenging heterocyclic and polyfluorinated aromatic substrates can be employed

  在环境温度或低催化剂负载量下，通过钯催化的根岸交叉偶联合成了多种联芳基化合物。该协议的特点是使用最近报道的氨基联苯钯环预催化剂来生成具有催化活性的 XPhosPd 0物质。值得注意的是，可以采用各种具有挑战性的杂环和多氟化芳香族底物来获得高产率的产品。
• Activation of reducing agents. Sodium hydride containing complex reducing agents. 32. NiCRAL's as very efficient agents in promoting cross-coupling of aryl halides
  作者：Mouhsine Lourak、Regis Vanderesse、Yves Fort、Paul Caubere

  DOI：10.1021/jo00281a028

  日期：1989.9