4-(2,5-difluorophenyl)pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(2,5-difluorophenyl)pyridine
• 化学式: C₁₁H₇F₂N
• 分子量: 191.18
• InChiKey: GPHIDODIJGSPDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-碘吡啶 、 1,4-二氟苯 在 1,10-菲罗啉 、 potassium tert-butylate 作用下， 反应 3.0h， 以44%的产率得到4-(2,5-difluorophenyl)pyridine
  参考文献：
  名称：

  Simple and expedient metal-free CH-functionalization of fluoro-arenes by the BHAS method – Scope and limitations

  摘要：

  We report here the facile substitution of aromatic iodides with non-activated fluoroarenes through radical-promoted reaction conditions. Applying the recently-popularized BHAS methodology, catalytic 1,10-phenanthroline and KOtBu and the desired fluorobenzene as reactant and solvent, various fluorinated biaryls can be synthesized in moderate to good yields. The method provides a simple access to generate potentially many 'FnAr'-substituted derivatives from a single haloarene synthetic intermediate, using relatively cheap and non-toxic fluoroarene substrates directly from the bottle, and may therefore be of use for medicinal chemistry campaigns. Although the method has a limitation in that it is not compatible with substrates featuring base-sensitive substituents, especially 1,4-difluorobiaryls are accessible in good yields. These investigations facilitate the exploitation of the potential of this protocol to synthesize biologically active fluorinated biaryls, e.g. WNT-active molecules. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.06.010

文献信息

• Simple and expedient metal-free CH-functionalization of fluoro-arenes by the BHAS method – Scope and limitations
  作者：Stephanie Lindner、Stefan Bräse、Kye-Simeon Masters

  DOI：10.1016/j.jfluchem.2015.06.010

  日期：2015.11

  We report here the facile substitution of aromatic iodides with non-activated fluoroarenes through radical-promoted reaction conditions. Applying the recently-popularized BHAS methodology, catalytic 1,10-phenanthroline and KOtBu and the desired fluorobenzene as reactant and solvent, various fluorinated biaryls can be synthesized in moderate to good yields. The method provides a simple access to generate potentially many 'FnAr'-substituted derivatives from a single haloarene synthetic intermediate, using relatively cheap and non-toxic fluoroarene substrates directly from the bottle, and may therefore be of use for medicinal chemistry campaigns. Although the method has a limitation in that it is not compatible with substrates featuring base-sensitive substituents, especially 1,4-difluorobiaryls are accessible in good yields. These investigations facilitate the exploitation of the potential of this protocol to synthesize biologically active fluorinated biaryls, e.g. WNT-active molecules. (C) 2015 Elsevier B.V. All rights reserved.