1,2,3,4,5-五氟-6-(2-氟苯基)苯 | 41877-27-4

• 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: 1,2,3,4,5-五氟-6-(2-氟苯基)苯
• 英文名称: 2,2',3,4,5,6-hexafluoro-1,1'-biphenyl
• 英文别名: 1,2,3,4,5-pentafluoro-6-(2-fluorophenyl)benzene
• CAS: 41877-27-4
• 化学式: C₁₂H₄F₆
• 分子量: 262.154
• InChiKey: VPBBMLNMHNDQOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  57-59 °C(Solv: chloroform (67-66-3))
• 沸点：
  223.6±35.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻溴氟苯 、 五氟苯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 potassium carbonate 作用下， 以 醋酸异丙酯 为溶剂， 反应 12.0h， 以99%的产率得到1,2,3,4,5-五氟-6-(2-氟苯基)苯
  参考文献：
  名称：

  Mild and General Conditions for the Cross-Coupling of Aryl Halides with Pentafluorobenzene and Other Perfluoroaromatics

  摘要：

  New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.

  DOI：

  10.1021/ol0619967

文献信息

• Copper-Catalyzed Decarboxylative Cross-Coupling of Potassium Polyfluorobenzoates with Aryl Iodides and Bromides
  作者：Rui Shang、Yao Fu、Yan Wang、Qing Xu、Hai-Zhu Yu、Lei Liu

  DOI：10.1002/anie.200904916

  日期：2009.11.23

  For copper only: The decarboxylative cross‐coupling of readily accessible and nonvolatile potassium polyfluorobenzoates with aryl iodides and bromides using a copper catalyst provides polyfluorobiaryls and polyfluorostilbenes in excellent yields (see scheme). Mechanistic analyses are reported for the title reaction.

  仅适用于铜：使用铜催化剂，易于获得且不挥发的多氟苯甲酸钾与芳基碘化物和溴化物的脱羧交叉偶联可提供极佳的收率的多氟联芳基和多氟苯磺酸酯（请参见方案）。报告了标题反应的机理分析。
• Transition‐Metal‐Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles
  作者：Lucie Finck、Martin Oestreich

  DOI：10.1002/chem.202101731

  日期：2021.8.2

  coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N’-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (SNAr). These reactions typically proceed at room temperature

  报道了足够缺电子的氟化芳烃和官能化的N-芳基-N'-甲硅烷基二氮烯作为掩蔽的芳基亲核试剂的化学选择性 C(sp 2 )-C(sp 2 ) 偶联。氟化物促进的转化涉及原位生成用各种敏感官能团修饰的芳基亲核试剂，然后逐步进行亲核芳族取代 (S N Ar)。这些反应通常在室温下在几分钟内进行。这种催化过程允许两个偶联伙伴的功能化，以良好的产率提供高度氟化的联芳基化合物。
• Copper-catalyzed arylstannylation of arynes in a sequence
  作者：Hideya Tanaka、Hitoshi Kuriki、Teruhiko Kubo、Itaru Osaka、Hiroto Yoshida

  DOI：10.1039/c9cc02738f

  日期：——

  Copper-catalyzed arylstannylation of arynes has been developed. This transformation enables variously substituted ortho-stannylbiaryls and teraryls to be constructed straightforwardly. An electron-deficient tin center is the key, and thus the single or dual insertion of arynes into arylstannanes is precisely controllable by simply changing the equivalence of aryne precursors.

  已经开发了铜催化的芳烃的芳基甲锡烷基化。该转化使得可以直接构建各种取代的邻-锡烷基二芳基和三芳基。缺电子的锡中心是关键，因此，只需简单地改变芳烃前体的当量，即可精确控制芳烃单芳基或双芳烃的插入。
• Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis
  作者：Andreas U. Meyer、Tomáš Slanina、Chang-Jiang Yao、Burkhard König

  DOI：10.1021/acscatal.5b02410

  日期：2016.1.4

  Visible light and eosin Y catalyze the direct arylation of simple arenes with fluorinated aryl bromides by a photoredox process. The reaction scope is broad in fluorinated compounds and arenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable polyfluorinated biaryl structures. The mild reaction conditions allow a selective reaction with

  可见光和曙红Y通过光氧化还原过程催化简单的芳烃与氟化的芳基溴化物直接芳基化。反应范围在氟化化合物和芳烃中很宽，常规和简单的方法为合成有价值的多氟化联芳基结构提供了一种无金属的替代方法。温和的反应条件允许在不保护官能团的情况下与生物碱马钱子碱进行选择性反应，从而说明该方法可用于后期功能化。机理研究表明，曙红Y通过三乙胺通过三重态状态进行光还原，随后电子从曙红Y自由基阴离子转移到多氟溴芳烃，后者分裂成多氟芳基自由基和溴化阴离子。
• Reactions of pentafluorophenylxenon(II) hexafluoroarsenate [C6F5Xe]+[AsF6]− with aromatic compounds
  作者：H.J. Frohn、A. Klose、V.V. Bardin

  DOI：10.1016/s0022-1139(00)80556-4

  日期：1993.10

  Pentafluorophenylxenon(II) hexafluoroarsenate [C6F5Xe]+[AsF6]− reacts (MeCN, 20 °C) with aromatic compounds C6H5X (X = CH3, F, CF3, NO2 and CN), yielding isomeric mixtures of polyfluorinated biphenyls XC6H4C6F5. When X = I, iodopentafluorobenzene is formed in addition, whereas trimethylsilylbenzene (X = SiMe3) is only converted to C6H5C6F5 and C6F5H. These results are compared with the data for the

  六氟砷酸五氟苯基氙（II）[C 6 F 5 Xe] + [AsF 6 ] -（MeCN，20°C）与芳族化合物C 6 H 5 X（X = CH 3，F，CF 3，NO 2和CN）反应，得到多氟联苯XC 6 H 4 C 6 F 5的异构体混合物。当X ＝ 1时，另外形成碘五氟苯，而三甲基甲硅烷基苯（X ＝ SiMe 3）仅转化为C 6 H 5 C 6 F 5和C。6个˚F 5 H.这些结果与用于与氟化氙相应的芳族化合物的基团和pentafluorophenylation氟化反应的数据相比较2。在以下条件下，多氟芳族化合物C 6 F 6，C 6 F 5 H，C 6 F 5 I，C 6 F 5 CN和C 6 F 5 SiMe 3不与[C 6 F 5 Xe] + [AsF 6 ] -反应。相同的条件。