2-(2-(fluorodiphenylsilyl)-4-methoxyphenyl)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-(2-(fluorodiphenylsilyl)-4-methoxyphenyl)pyridine
• 英文别名: Fluoro-(5-methoxy-2-pyridin-2-ylphenyl)-diphenylsilane；fluoro-(5-methoxy-2-pyridin-2-ylphenyl)-diphenylsilane
• 化学式: C₂₄H₂₀FNOSi
• 分子量: 385.513
• InChiKey: DNPLBXVEIHILIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基苯基)吡啶 、 Fluor-diphenylsilan 在 降冰片烯 、 iridium(I)-(1,5-cyclooctadiene)-acetylacetonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以78%的产率得到2-(2-(fluorodiphenylsilyl)-4-methoxyphenyl)pyridine
  参考文献：
  名称：

  Iridium-Catalyzed ortho-Selective C–H Silylation of Aromatic Compounds Directed toward the Synthesis of π-Conjugated Molecules with Lewis Acid–Base Interaction

  摘要：

  We successfully developed an iridium-catalyzed ortho-selective C-H silylation of aromatic compounds. The reaction exhibited a wide substrate scope, and a variety of pi-conjugated molecules were synthesized in good to excellent yields, even in gram scale. Several silyl groups could also be introduced into the products. The experimental results indicated that the regioselectivity could be controlled by a Lewis acid-base interaction between the Lewis acidic silicon atoms of fluorinated hydrosilanes and the Lewis basic nitrogen atoms of aromatic compounds.

  DOI：

  10.1021/acs.orglett.5b00529

文献信息

• Palladium-Catalyzed CH Fluorosilylation of 2-Phenylpyridines: Synthesis of Silafluorene Equivalents
  作者：Qing Xiao、Xiangtai Meng、Motomu Kanai、Yoichiro Kuninobu

  DOI：10.1002/anie.201310293

  日期：2014.3.17

  2‐dioxaborolan‐2‐yl)diphenylsilane produced fluorosilylated 2‐phenylpyridines in good to excellent yields under palladium catalysis. This reaction is the first example of CH fluorosilylation. Single‐crystal X‐ray structure analysis revealed a Lewis acid–base interaction between the silicon and nitrogen atoms, and the obtained fluorosilylated products are silafluorene equivalents. The fluorosilylated products

  用氨基（1,3,2-二氧杂硼硼烷-2-基）二苯基硅烷处理2-苯基吡啶产生的氟硅烷化2-苯基吡啶在钯催化下具有良好至极佳的收率。该反应是C的第一示例 ħfluorosilylation。X射线单晶结构分析表明，硅和氮原子之间存在路易斯酸碱相互作用，所获得的氟硅烷化产物为硅芴等同物。氟硅烷化产物显示出比相应的硅芴衍生物更强的荧光。
• Iridium-Catalyzed <i>ortho</i>-Selective C–H Silylation of Aromatic Compounds Directed toward the Synthesis of π-Conjugated Molecules with Lewis Acid–Base Interaction
  作者：Takayuki Wakaki、Motomu Kanai、Yoichiro Kuninobu

  DOI：10.1021/acs.orglett.5b00529

  日期：2015.4.3

  We successfully developed an iridium-catalyzed ortho-selective C-H silylation of aromatic compounds. The reaction exhibited a wide substrate scope, and a variety of pi-conjugated molecules were synthesized in good to excellent yields, even in gram scale. Several silyl groups could also be introduced into the products. The experimental results indicated that the regioselectivity could be controlled by a Lewis acid-base interaction between the Lewis acidic silicon atoms of fluorinated hydrosilanes and the Lewis basic nitrogen atoms of aromatic compounds.