2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)pyridine | 1422200-14-3

• 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: 2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)pyridine
• CAS: 1422200-14-3
• 化学式: C₁₂H₇F₄NO
• 分子量: 257.187
• InChiKey: DEZCKKCCPPCOFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯并恶唑 、 2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)pyridine 在 双(乙腈)氯化钯(II) 、 lithium tert-butoxide 、 1,2-双(二苯基膦基)苯 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以60%的产率得到2-(2,4,5-trifluoro-3-methoxy-6-(pyridin-2-yl)phenyl)benzoxazole
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of Polyfluorinated Arenes with Heteroarenes via C–F/C–H Activation

  摘要：

  The first palladium-catalyzed coupling of 2-pyrldyl-polyfluoroarenes and benzoxazole, thiazole, benzothiazole, benzoimidazole, oxazole or oxadiazole via a concurrent C-F/C-H activation is described. Initial mechanistic studies showed that C-F activation of perfluoroarene is likely the rate-limiting step of the catalytic cycle. This protocol provides a useful and operationally simple process to functionalized polyfluoroarenes.

  DOI：

  10.1021/ol303567t
• 作为产物：
  描述：

  2-溴吡啶 在 potassium phosphate 、 copper(l) iodide 、 1,10-菲罗啉 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)pyridine
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of Polyfluorinated Arenes with Heteroarenes via C–F/C–H Activation

  摘要：

  The first palladium-catalyzed coupling of 2-pyrldyl-polyfluoroarenes and benzoxazole, thiazole, benzothiazole, benzoimidazole, oxazole or oxadiazole via a concurrent C-F/C-H activation is described. Initial mechanistic studies showed that C-F activation of perfluoroarene is likely the rate-limiting step of the catalytic cycle. This protocol provides a useful and operationally simple process to functionalized polyfluoroarenes.

  DOI：

  10.1021/ol303567t

文献信息

• Rhodium-Catalyzed<i>ortho</i>-Selective CF Bond Borylation of Polyfluoroarenes with BpinBpin
  作者：Wen-Hao Guo、Qiao-Qiao Min、Ji-Wei Gu、Xingang Zhang

  DOI：10.1002/anie.201500124

  日期：2015.7.27

  An ortho‐selective CF bond borylation between N‐heterocycle‐substituted polyfluoroarenes and Bpin‐Bpin with simple and commercially available [Rh(cod)2]BF4 as a catalyst is now reported. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, even toward monofluoroarene, thus providing a facile access to a wide range of borylated fluoroarenes that are useful

  邻选择性Ç 的N-杂环取代的polyfluoroarenes和BPIN-BPIN用简单的和可商购的间F键硼化的[Rh（COD）2 ] BF 4现在报告作为催化剂。该反应在温和的反应条件下以高效率和宽泛的底物范围进行，甚至朝单氟芳烃进行，因此可以轻松地获得各种对光电子材料有用的硼化氟代芳烃。初步的机理研究表明，通过关键中间体氢化铑（III）络合物[（H）Rh III L n（BPIn）]的Rh III / V催化循环可能参与了反应。
• Nickel-catalyzed reductive cross-coupling of polyfluoroarenes with alkyl electrophiles by site-selective C–F bond activation
  作者：Longlong Xi、Liting Du、Zhuangzhi Shi

  DOI：10.1016/j.cclet.2022.01.077

  日期：2022.9

  A nickel-catalyzed reductive cross-coupling reactions between polyfluoroarenes and alkyl electrophiles is reported to access substituted fluoroarenes through chelation-assisted C–F activation. Diverse primary and secondary alkyl (pseudo)halides can be employed to couple with polyfluoroarenes, showing excellent regioselectivity. Furthermore, the nickel-catalyzed asymmetric cross-coupling of polyfluoroarenes

  据报道，多氟芳烃和烷基亲电试剂之间的镍催化还原交叉偶联反应通过螯合辅助的 C-F 活化获得取代的氟芳烃。多种伯和仲烷基（假）卤化物可用于与多氟芳烃偶联，表现出优异的区域选择性。此外，初步探索了镍催化的多氟芳烃与外消旋烷基卤化物的不对称交叉偶联。此外，还以losmapimod及其类似物的全合成为关键步骤，证明了题名转换的实用性。所开发的方法具有许多优点，包括经济的催化系统、可商购的烷基亲电试剂以及缺乏敏感的有机金属试剂。