2,2'-(fluoro(phenyl)methylene)dipyridine | 1316276-72-8

• 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'-(fluoro(phenyl)methylene)dipyridine
• 英文别名: 2-(fluoro-phenyl-pyridin-2-ylmethyl)pyridine
• CAS: 1316276-72-8
• 化学式: C₁₇H₁₃FN₂
• 分子量: 264.302
• InChiKey: LTPQBGVWVNMROI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2'-(fluoro(phenyl)methylene)dipyridine 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 (2,2'-(fluoro(phenyl)methylene)dipyridine)Ni^IV(CF₃)₂F
  参考文献：
  名称：

  Oxidatively Induced C–H Activation at High Valent Nickel

  摘要：

  This communication describes a series of oxidatively induced intramolecular arene C-H activation reactions of Ni-II model complexes to yield Ni-IV sigma-aryl products. These reactions proceed within to min at room temperature, which represents among the mildest conditions reported for C-H cleavage at a Ni center. A combination of density functional theory and preliminary experimental mechanistic studies implicate a pathway involving initial 2e(-) oxidation of the Ni-II starting materials by the transfer reagent N-fluoro-2,4,6-trimethylpyr-idinium triflate followed by triflate-assisted C-H cleavage at Ni-IV to yield the products.

  DOI：

  10.1021/jacs.7b02387
• 作为产物：
  描述：

  2-二吡啶基酮 在 二乙胺基三氟化硫 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 2,2'-(fluoro(phenyl)methylene)dipyridine
  参考文献：
  名称：

  Oxidatively Induced C–H Activation at High Valent Nickel

  摘要：

  This communication describes a series of oxidatively induced intramolecular arene C-H activation reactions of Ni-II model complexes to yield Ni-IV sigma-aryl products. These reactions proceed within to min at room temperature, which represents among the mildest conditions reported for C-H cleavage at a Ni center. A combination of density functional theory and preliminary experimental mechanistic studies implicate a pathway involving initial 2e(-) oxidation of the Ni-II starting materials by the transfer reagent N-fluoro-2,4,6-trimethylpyr-idinium triflate followed by triflate-assisted C-H cleavage at Ni-IV to yield the products.

  DOI：

  10.1021/jacs.7b02387

文献信息

• Charge Delocalization and Enhanced Acidity in Tricationic Superelectrophiles
  作者：Rajasekhar Reddy Naredla、Chong Zheng、Sten O. Nilsson Lill、Douglas A. Klumpp

  DOI：10.1021/ja2046364

  日期：2011.8.24

  This Article presents the results from studies related to the chemistry of tricationic superelectrophiles. A series of triaryl methanols were ionized in Bronsted superacids, and the corresponding tricationic intermediates were formed. The trications are found to participate in two types of reactions; both are characteristic of highly charged organic cations. One set of reactions occurs through charge migration. A second set of reactions occurs through deprotonation of an unusually acidic site on the tricationic species. One of the tricationic intermediates has been directly observed by low temperature NMR spectroscopy. These highly charged ions and their reactions have also been studied using density functional theory calculations. As a result of charge migration, electron density at a carbocation site is found to increase with progression from monocationic to pentacationic structures.