5-Fluoro-2-[(3-methylphenyl)methyl]pyridine | 1052101-62-8

• 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: 5-Fluoro-2-[(3-methylphenyl)methyl]pyridine
• CAS: 1052101-62-8
• 化学式: C₁₃H₁₂FN
• 分子量: 201.243
• InChiKey: RBICWIJCXVBTSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘苯二乙酸 、 5-Fluoro-2-[(3-methylphenyl)methyl]pyridine 在 palladium diacetate 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 生成 [2-[(5-Fluoropyridin-2-yl)methyl]-4-methylphenyl] acetate
  参考文献：
  名称：

  Insights into Directing Group Ability in Palladium-Catalyzed C−H Bond Functionalization

  摘要：

  This paper describes a detailed investigation of factors controlling the dominance of a directing group in Pd-catalyzed ligand-directed arene acetoxylation. Mechanistic studies, involving reaction kinetics, Hammett analysis, kinetic isotope effect experiments, and the kinetic order in oxidant, have been conducted for a series of different substrates. Initial rates studies of substrates bearing different directing groups showed that these transformations are accelerated by the use of electron-withdrawing directing groups. However, in contrast, under conditions where two directing groups are in competition with one another in the same reaction flask, substrates with electron-donating directing groups react preferentially. These results are discussed in the context of the proposed mechanism for Pd-catalyzed arene acetoxylation.

  DOI：

  10.1021/ja8045519
• 作为产物：
  描述：

  bromozinc(1+),1-methanidyl-3-methylbenzene 、 alkaline earth salt of/the/ methylsulfuric acid 在 palladium diacetate 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 生成 5-Fluoro-2-[(3-methylphenyl)methyl]pyridine
  参考文献：
  名称：

  Insights into Directing Group Ability in Palladium-Catalyzed C−H Bond Functionalization

  摘要：

  This paper describes a detailed investigation of factors controlling the dominance of a directing group in Pd-catalyzed ligand-directed arene acetoxylation. Mechanistic studies, involving reaction kinetics, Hammett analysis, kinetic isotope effect experiments, and the kinetic order in oxidant, have been conducted for a series of different substrates. Initial rates studies of substrates bearing different directing groups showed that these transformations are accelerated by the use of electron-withdrawing directing groups. However, in contrast, under conditions where two directing groups are in competition with one another in the same reaction flask, substrates with electron-donating directing groups react preferentially. These results are discussed in the context of the proposed mechanism for Pd-catalyzed arene acetoxylation.

  DOI：

  10.1021/ja8045519

文献信息

• Metal-free directed C−H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines
  作者：Gaorong Wu、Xiaobo Xu、Shuai Wang、Lu Chen、Binghan Pang、Tao Ma、Yafei Ji

  DOI：10.1016/j.cclet.2021.09.081

  日期：2022.4

  A novel method for metal-free C−H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines has been reported. The 5-fluoropyridine directed borylation reaction exhibited high efficiency and site exclusivity. The useful protocol could be executed on a gram-scale easily and the borylated products showed good derivatization applications. Moreover, the practicality of the strategy

  报道了一种用于 2-( N-甲基苯胺基)-5-氟吡啶和 2-苄基-5-氟吡啶的无金属 C-H 硼化的新方法。5-氟吡啶定向硼化反应表现出高效率和位点排他性。有用的协议可以轻松地在克级上执行，并且硼化产物显示出良好的衍生化应用。此外，该策略的实用性因指导基团可以以可接受的产量移除而得到扩展。