1,3-di-(p-tolyl)-2,4,5,6-tetrafluorobenzene

• 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: 1,3-di-(p-tolyl)-2,4,5,6-tetrafluorobenzene
• 英文别名: 1,2,3,5-Tetrafluoro-4,6-bis(4-methylphenyl)benzene；1,2,3,5-tetrafluoro-4,6-bis(4-methylphenyl)benzene
• 化学式: C₂₀H₁₄F₄
• 分子量: 330.325
• InChiKey: OUXIVQOOWDQJGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-碘甲苯 、 1,2,3,5-四氟苯 在 copper(l) iodide 、 1,10-菲罗啉 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以73%的产率得到2,3,4,6-tetrafluoro-4'-methyl-biphenyl
  参考文献：
  名称：

  Copper-Catalyzed Arylation and Alkenylation of Polyfluoroarene C−H Bonds

  摘要：

  An efficient, copper-catalyzed method for the arylation, alkenylation, and benzylation of polyfluoroarenes has been developed. Arenes containing two or more fluorine substituents on the aromatic ring can be efficiently functionalized. The best results are obtained by using a combination of copper iodide catalyst, phenanthroline ligand, aryl bromide or aryl iodide coupling partner, and DMF or DMF/xylene mixed solvent.

  DOI：

  10.1021/ja077862l

文献信息

• COPPER-CATALYZED C-H BOND ARYLATION
  申请人：Daugulis Olafs

  公开号：US20090076266A1

  公开（公告）日：2009-03-19

  The present invention is a one-step method for efficiently converting carbon-hydrogen bonds into carbon-carbon bonds using a combination of aryl halides, a substrate, and a copper salt as catalyst. This method allows faster introduction of complex molecular entities, a process that would otherwise require many more steps. This invention is particularly relevant for the organic synthesis of complex molecules such as, but not limited to, pharmacophores and explosives.

  本发明是一种一步法，通过使用芳基卤化物、底物和铜盐作为催化剂，高效地将碳氢键转化为碳碳键的方法。该方法允许更快地引入复杂的分子实体，否则这个过程需要更多步骤。该发明特别适用于有机合成中复杂分子的合成，例如药用分子和爆炸物等。
• Palladium‐Catalyzed Carbon–Fluorine and Carbon–Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes
  作者：Wenyi Chen、Thomas N. Hooper、Jamues Ng、Andrew J. P. White、Mark R. Crimmin

  DOI：10.1002/anie.201706378

  日期：2017.10.2

  complex was identified as a catalyst for the selective transformation of sp2C−F and sp2C−H bonds of fluoroarenes and heteroarenes to sp2C−Al bonds (19 examples, 1 mol % Pd loading). The carbon–fluorine bond functionalization reaction is highly selective for the formation of organoaluminium products in preference to hydrodefluorination products (selectivity=4.4:1 to 27:1). Evidence is presented for a tandem

  通过偶然发现，钯双（膦）配合物被鉴定为将氟代芳烃的sp 2 C-F和sp 2 C-H键选择性转化为sp 2 C-Al键的催化剂（19个例子，1 mol钯含量百分比）。碳-氟键官能化反应对有机铝产物的形成具有高度选择性，而不是氢脱氟产物（选择性= 4.4：1至27：1）。提出了串联催化过程的证据，其中加氢脱氟化后是sp 2 C-H铝化。
• Catalytic Intermolecular Direct Arylation of Perfluorobenzenes
  作者：Marc Lafrance、Christopher N. Rowley、Tom K. Woo、Keith Fagnou

  DOI：10.1021/ja062509l

  日期：2006.7.1

  Penta-, tetra-, tri-, and difluorobenzenes undergo direct arylation with a wide range of arylhalides in high yield. Inverse reactivity is observed compared to the common electrophilic aromatic substitution pathway since electron-deficient, C-H acidic arenes react preferentially. Computational studies indicate that C-H bond cleavage occurs via a concerted carbon-palladium and carbon-hydrogen bond cleaving event involving a carbonate or a bromide ligand. The reactions are rapid, require only a slight excess of the perfluoroarene reagent, and utilize commercially available, air-stable catalyst precursors.
• Hetero-dicarbene Complexes of Palladium(II): Syntheses and Catalytic Activities
  作者：Dan Yuan、Han Vinh Huynh

  DOI：10.1021/om500659v

  日期：2014.11.10

  A series of Pd(II) dibromido complexes 2-6 bearing cis-chelating hetero-dicarbenes, which contain two different types of NHCs linked by a propylene chain, have been synthesized. In most cases, the N-methylbenzimidazolin-2-ylidene moiety was kept as one NHC donor, while the other one varies with different heterocyclic backbones. As an exception, the hetero-diNHC in complex 8 is derived by combining 1,2,4-triazole and indazole precursors instead. Analogous complexes 9-17, carrying more labile CF3CO2 or CH3CN ligands, were synthesized by reacting the aforementioned bromido complexes with AgO2CCF3 or AgOTf in CH3CN. A systematic catalytic comparison of 9-17 in the direct arylation of pentafluorobenzene with 4-chlorobromobenzene was carried out, and complexes that contain bulkier and less electron-donating ligands were found to be more active. Complex 12, carrying the mesitylimidazolin-2-ylidene unit, proved to be the most efficient, and its activity was also tested in the direct arylation of tetrafluorobenzenes.
• US8952207B2
  申请人：——

  公开号：US8952207B2

  公开（公告）日：2015-02-10