2-(4-tert-butoxy-2,3,5,6-tetrafluorophenyl)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: 2-(4-tert-butoxy-2,3,5,6-tetrafluorophenyl)pyridine
• 英文别名: 2-(2,3,5,6-tetrafluoro-4-t-butoxyphenyl)pyridine；2-[2,3,5,6-Tetrafluoro-4-[(2-methylpropan-2-yl)oxy]phenyl]pyridine
• 化学式: C₁₅H₁₃F₄NO
• 分子量: 299.268
• InChiKey: IELMKIISBOCKBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-(4-tert-butoxy-2,3,5,6-tetrafluorophenyl)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39%的产率得到2-(3-tert-butoxy-2,4,5-trifluoro-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 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 17.0h， 生成 2-(4-tert-butoxy-2,3,5,6-tetrafluorophenyl)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

• 2-(Fluorophenyl)pyridines by the Suzuki–Miyaura method: Ag2O accelerates coupling over undesired ipso substitution (SNAr) of fluorine
  作者：Jing Chen、Arthur Cammers-Goodwin

  DOI：10.1016/s0040-4039(02)02793-4

  日期：2003.2

  Problematic ipso substitution was observed in the Suzuki-Miyaura coupling of pentafluorophenylboronic acid to make 2-pentafluorophenylpyridine. Strong bases favored coupling, but under these conditions fluorine in the product tended to undergo nucleophilic substitution. Inclusion of Ag2O accelerated coupling over ipso substitution. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Palladium-Catalyzed Coupling of Polyfluorinated Arenes with Heteroarenes via C–F/C–H Activation
  作者：Daohong Yu、Long Lu、Qilong Shen

  DOI：10.1021/ol303567t

  日期：2013.2.15

  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.