2-biphenyl-4-yl-5-(trifluoromethyl)pyridine | 1101205-35-9

• 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-biphenyl-4-yl-5-(trifluoromethyl)pyridine
• 英文别名: 2-(4-Phenylphenyl)-4-(trifluoromethyl)pyridine
• CAS: 1101205-35-9
• 化学式: C₁₈H₁₂F₃N
• 分子量: 299.295
• InChiKey: WEAKZFDASDIFFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴代联苯 、 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyridine 在 1,1'-bis(diphenylphosphino)ferrocene 、 palladium diacetate 、 caesium carbonate 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以94%的产率得到2-biphenyl-4-yl-5-(trifluoromethyl)pyridine
  参考文献：
  名称：

  Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates

  摘要：

  The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(l) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope Is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.

  DOI：

  10.1021/ol802556f

文献信息

• Ceramic boron carbonitrides for unlocking organic halides with visible light
  作者：Tao Yuan、Meifang Zheng、Markus Antonietti、Xinchen Wang

  DOI：10.1039/d1sc01028j

  日期：——

  halides, with visible light irradiation. Cross-coupling of halides to afford new C–H, C–C, and C–S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C–X (carbon–halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only

  光化学通过电子转移过程从底物中诱导自由基中间体，为有机转化提供了可持续的途径。然而，进展受到多相光催化剂的限制，这些光催化剂需要高效、稳定、廉价才能长期运行，并且易于回收和产品分离。在这里，我们报道碳氮化硼（BCN）陶瓷就是这样一个系统，可以在可见光照射下减少有机卤化物，包括（杂）芳基和烷基卤化物。卤化物的交叉偶联可在环境反应条件下进行，以提供新的 C-H、C-C 和 C-S 键。在没有任何金属基催化剂或配体的情况下，通过介晶 C-X（碳-卤素）键断裂将氢、（杂）芳基和磺酰基引入芳烃和杂芳烃的设计位置。 BCN不仅可用于半反应，例如与牺牲剂的还原反应，还可用于通过氧化和还原界面电子转移的氧化还原反应。 BCN 光催化剂表现出对不同取代基的耐受性，并且在五次回收后活性保持不变。这种表面上不含金属的系统为使用光能和可持续材料的各种有机催化剂开辟了新的机遇，这些催化剂不含金属、廉价且稳定。
• Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates
  作者：James Z. Deng、Daniel V. Paone、Anthony T. Ginnetti、Hideki Kurihara、Spencer D. Dreher、Steven A. Weissman、Shaun R. Stauffer、Christopher S. Burgey

  DOI：10.1021/ol802556f

  日期：2009.1.15

  The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(l) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope Is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.