2,3,4,5-四氟-6-硝基联苯 | 29636-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,3,4,5-四氟-6-硝基联苯
• 英文名称: 2,3,4,5-tetrafluoro-6-nitrobiphenyl
• 英文别名: 3.4.5.6-Tetrafluor-2-nitro-biphenyl；1,2,3,4-tetrafluoro-5-nitro-6-phenylbenzene
• CAS: 29636-82-6
• 化学式: C₁₂H₅F₄NO₂
• 分子量: 271.171
• InChiKey: NETVRRVCAFKKJD-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C(Solv: hexane (110-54-3))
• 沸点：
  321.5±37.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4,5-四氟硝基苯 、 苯 在 2,2'-硫代二丙烷 、 palladium diacetate 、 溶剂黄146 、 silver carbonate 作用下， 反应 20.0h， 以82%的产率得到2,3,4,5-四氟-6-硝基联苯
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Polyfluoroarenes with Simple Arenes

  摘要：

  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.

  DOI：

  10.1021/ol102688e

文献信息

• Highly Selective Pd-Catalyzed Direct C–F Bond Arylation of Polyfluoroarenes
  作者：Zhi-Ji Luo、Hai-Yang Zhao、Xingang Zhang

  DOI：10.1021/acs.orglett.8b00692

  日期：2018.5.4

  A directing-group-free palladium-catalyzed direct arylation of simple polyfluoroarenes with arylboronic acids through selective C–F bond activation is described. The combination of Pd(OAc)2 with BrettPhos was identified as an efficient catalytic system to promote the reaction with high regioselectivity and broad substrate scope. Preliminary mechanistic studies reveal that the oxidative addition of

  描述了通过选择性CF键活化，无直接基团的钯催化的简单多氟芳烃与芳基硼酸的直接芳基化。Pd（OAc）2与BrettPhos的结合被认为是一种有效的催化体系，具有高区域选择性和广泛的底物范围，可促进反应。初步的机理研究表明，Pd在C-F键上的氧化加成参与了催化循环。
• Palladium-Catalyzed C−F Activation of Polyfluoronitrobenzene Derivatives in Suzuki−Miyaura Coupling Reactions
  作者：Matthew R. Cargill、Graham Sandford、Andrezj J. Tadeusiak、Dmitrii S. Yufit、Judith A. K. Howard、Pinar Kilickiran、Gabrielle Nelles

  DOI：10.1021/jo100877j

  日期：2010.9.3

  substrates for palladium-catalyzed C−F bond arylation using readily available palladium catalysts under both conventional heating and microwave conditions. Arylation occurs ortho to the nitro group offering a synthetic route to polyfluorinated 2-arylnitrobenzene systems. The regiochemistry of the arylation reactions suggests that there is a significant directing interaction between the nitro group and the incoming

  高度氟化的硝基苯衍生物是在常规加热和微波条件下使用易于获得的钯催化剂进行钯催化的C-F键芳基化的合适底物。芳基化发生在邻位到硝基上，为合成多氟2-芳基硝基苯系统提供了一条合成途径。芳基化反应的区域化学表明，在硝基和进入的亲核钯催化剂之间存在显着的直接相互作用，这是由于在环上存在几个氟原子而促进的。对几种四氟和三氟硝基苯衍生物的区域选择性和反应性的研究，为氧化加成步骤的高度亲核特性提供了进一步的证据，这与涉及芳基碘化物和溴化物的更常规的Suzuki-Miyaura偶联反应的协同机理相反。
• Homolytic reactions of perfluoroaromatic compounds. Part III. Reactions of benzoyl peroxide with hexafluorobenzene, chloro-, bromo-, and nitro-pentafluorobenzene, and pentafluoropyridine
  作者：P. H. Oldham、Gareth H. Williams、Barbara A. Wilson

  DOI：10.1039/j29700001346

  日期：——

  The reaction of benzoyl peroxide with hexafluorobenzene has been shown to give 2,3,4,5,6-pentafluorobiphenyl and a residue whose relative yields depend mainly on the conditions used for the distillation of the biaryl from the reaction mixtures. This supports the suggestion made previously that the biaryl is formed partly by defluorination of σ-complexes during reaction, and partly by thermal breakdown

  已经显示过氧化苯甲酰与六氟苯的反应产生2,3,4,5,6-五氟联苯和其相对产率主要取决于用于从反应混合物中蒸馏联芳基的条件的残余物。这支持了先前提出的建议，即联芳基部分是通过在反应过程中σ配合物的脱氟，部分是通过在蒸馏过程中σ配合物的二聚体的热分解而形成的。氯，溴和硝基五氟苯与五氟吡啶的类似苯基化反应可得到异构体产物的混合物。已测量并讨论了这些异构体与氯和溴五氟苯和五氟吡啶形成的比例。
• 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.