3,4-dimethoxy-3'-trifluoromethylbiphenyl

• 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: 3,4-dimethoxy-3'-trifluoromethylbiphenyl
• 英文别名: 1,2-Dimethoxy-4-[3-(trifluoromethyl)phenyl]benzene；1,2-dimethoxy-4-[3-(trifluoromethyl)phenyl]benzene
• 化学式: C₁₅H₁₃F₃O₂
• 分子量: 282.262
• InChiKey: ACUWVDRCUXCXPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tetrafluoroborate of 3-trifluoromethylbenzenediazonium 、 3,4-二甲氧基苯硼酸 在 5% Pd/BaCO3 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以94%的产率得到3,4-dimethoxy-3'-trifluoromethylbiphenyl
  参考文献：
  名称：

  钯（0）/碳酸钡催化四氟硼酸亚芳基重氮盐与硼酸的高效，实用交叉偶联

  摘要：

  苯二氮杂四氟硼酸盐与硼酸的交叉偶联反应是由不寻常的钯（0）/碳酸钡催化剂催化的，被描述为经典均相条件的一种非常实用且高效的替代方法。反应在室温下在温和条件下进行，没有任何碱和配体。还展示了通过一锅法制备不对称三联苯的机会。最后，联苯吡嗪的合成突出了这种方法的力量。

  DOI：

  10.1002/adsc.200800025

文献信息

• A Highly Para-Selective Copper(II)-Catalyzed Direct Arylation of Aniline and Phenol Derivatives
  作者：Claire-Lise Ciana、Robert J. Phipps、Jochen R. Brandt、Falco-Magnus Meyer、Matthew J. Gaunt

  DOI：10.1002/anie.201004703

  日期：2011.1.10

  In short order: A copper‐catalyzed Friedel–Crafts‐type strategy has been developed for the title reaction. An iterative CH arylation strategy has also been demonstrated for the functionalization of anilines by sequentially delivering different aromatic groups to the para, ortho, and meta positions (see scheme, Bn=benzyl, Piv=pivaloyl).

  短期内：针对标题反应，开发了铜催化的Friedel-Crafts型策略。还已经证明了通过顺序地将不同的芳族基团依次传递到对位，邻位和间位来实现苯胺功能化的迭代CH芳基化策略（请参阅方案，Bn =苄基，Piv =新戊酰基）。
• Palladium-catalyzed decarbonylative Suzuki–Miyaura cross-coupling of amides by carbon–nitrogen bond activation
  作者：Tongliang Zhou、Chong-Lei Ji、Xin Hong、Michal Szostak

  DOI：10.1039/c9sc03169c

  日期：——

  cross-coupling or aryl halides is widely employed in the synthesis of many important molecules in synthetic chemistry, including pharmaceuticals, polymers and functional materials. Herein, we disclose the first palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides for the synthesis of biaryls through the selective activation of the N-C(O) bond of amides. This new method relies on

  钯催化的铃木-宫浦交叉偶联或芳基卤化物广泛应用于合成化学中许多重要分子的合成，包括药物、聚合物和功能材料。在此，我们公开了第一个钯催化的酰胺脱羰 Suzuki-Miyaura 交叉偶联，通过选择性活化酰胺的 NC(O) 键来合成联芳基化合物。这种新方法依赖于催化循环的精确序列工程，其中脱羰作用发生在金属转移步骤之前。该反应与多种硼酸和酰胺相容，以高产率提供有价值的联芳基化合物（> 60 个实例）。DFT 研究支持涉及氧化加成、脱羰和金属转移的机制，并提供了对高 NC(O) 键激活选择性的见解。最重要的是，该反应确立了钯催化在酰胺键的联芳铃木-宫浦交叉偶联中的应用，并且应该能够设计出多种交叉偶联方法，其中钯可与传统的由芳基卤化物合成联芳基和拟卤化物。
• Efficient and Practical Cross-Coupling of Arenediazonium Tetrafluoroborate Salts with Boronic Acids Catalyzed by Palladium(0)/Barium Carbonate
  作者：François-Xavier Felpin、Eric Fouquet

  DOI：10.1002/adsc.200800025

  日期：2008.4.7

  The cross-coupling reaction of arenediazonium tetrafluoroborate salts with boronic acids catalyzed by the unusual palladium(0)/barium carbonate catalyst is described as an extremely practical and highly efficient alternative to classical homogeneous conditions. Reactions are conducted under mild conditions at room temperature without any base and ligand. The opportunity of preparing unsymmetrical terphenyls

  苯二氮杂四氟硼酸盐与硼酸的交叉偶联反应是由不寻常的钯（0）/碳酸钡催化剂催化的，被描述为经典均相条件的一种非常实用且高效的替代方法。反应在室温下在温和条件下进行，没有任何碱和配体。还展示了通过一锅法制备不对称三联苯的机会。最后，联苯吡嗪的合成突出了这种方法的力量。
• Suzuki−Miyaura Reactions of Arenediazonium Salts Catalyzed by Pd(0)/C. One-Pot Chemoselective Double Cross-Coupling Reactions
  作者：Rachel H. Taylor、François-Xavier Felpin

  DOI：10.1021/ol0712733

  日期：2007.7.1

  Suzuki-Miyaura cross-coupling of arenediazonium tetrafluoroborate salts with boronic acid partners catalyzed by Pd(0)/C is described as a practical and efficient alternative to classical homogeneous conditions. Reactions conducted in alcoholic solvents proved to be extremely fast using mild conditions. Additionally, we developed a chemoselective double Suzuki-Miyaura cross-coupling in a single reaction

  Sduki-Miyaura由Pd（0）/ C催化的四氟硼酸二氮杂唑鎓盐与硼酸配偶体的交叉偶联被描述为经典均相条件的一种实用且有效的替代方法。在温和的条件下，在酒精溶剂中进行的反应非常快。此外，我们在单个反应容器中开发了化学选择性的双Suzuki-Miyaura交叉偶联，可合成不对称的三联苯。
• Improved Suzuki-Miyaura Reactions of Aryldiazonium Salts with Boronic Acids by Tuning Palladium on Charcoal Catalyst Properties
  作者：François-Xavier Felpin、Eric Fouquet、Cécile Zakri

  DOI：10.1002/adsc.200800783

  日期：2009.3

  Abstractmagnified imageAn improved Suzuki–Miyaura cross‐coupling reaction of aryldiazonium tetrafluoroborates with boronic acids catalyzed by a highly active palladium catalyst supported on charcoal is described as an extremely practical and efficient protocol. A properties‐activity study of various catalysts clearly established that the optimal catalytic activity was obtained with palladium nanoparticles having a low oxidation degree and uniformly dispersed on the charcoal. The optimized reaction conditions allow the cross‐coupling to proceed at room temperature without any base and ligand in technical grade methanol. Although the catalyst could not be recycled, the low palladium contamination of the solvent and product after a simple filtration of the palladium on charcoal (Pd/C) renders the present protocol competitive and safer for the environment compared to more conventional homogeneous conditions. We have highlighted the efficiency of this novel protocol by a short synthesis of the fungicide Boscalid®.