3-(fluoromethoxy)pyridine | 1551327-98-0

• 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: 3-(fluoromethoxy)pyridine
• 英文别名: 3-Fluoromethoxypyridine
• CAS: 1551327-98-0
• 化学式: C₆H₆FNO
• 分子量: 127.118
• InChiKey: KQWGNYJCLBBVFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  3-吡啶基氧乙酸乙酯 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 Selectfluor 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 3-(fluoromethoxy)pyridine
  参考文献：
  名称：

  Direct C–F Bond Formation Using Photoredox Catalysis

  摘要：

  We have developed the first example of a photoredox catalytic method for the formation of carbon-fluorine (C-F) bonds. The mechanism has been studied using transient absorption spectroscopy and involves a key single-electron transfer from the (MLCT)-M-3 (triplet metal-to-ligand charge transfer) state of Ru(bpy)(3)(2+) to Selectfluor. Not only does this represent a new reaction for photoredox catalysis, but the mild reaction conditions and use of visible light also make it a practical improvement over previously developed UV-mediated decarboxylative fluorinations.

  DOI：

  10.1021/ja412083f

文献信息

• Continuous Heterogeneous Photocatalysis in Serial Micro-Batch Reactors
  作者：Bartholomäus Pieber、Menny Shalom、Markus Antonietti、Peter H. Seeberger、Kerry Gilmore

  DOI：10.1002/anie.201712568

  日期：2018.7.26

  leaching catalysts, and heterogeneous photocatalysts are commonly employed in batch processes but are ill‐suited for continuous‐flow chemistry. Heterogeneous catalysts for thermal reactions are typically used in packed‐bed reactors, which cannot be penetrated by light and thus are not suitable for photocatalytic reactions involving solids. We demonstrate that serial micro‐batch reactors (SMBRs) allow

  批处理过程中通常使用固体试剂，浸出催化剂和非均相光催化剂，但不适用于连续流化学法。用于热反应的非均相催化剂通常用于填充床反应器中，该反应器不能被光穿透，因此不适用于涉及固体的光催化反应。我们证明了串联微间歇反应器（SMBR）可以连续利用固体材料以及流动中的液体和气体。该技术被用来开发选择性和有效的氟化反应，方法是使用改性的石墨碳氮化物非均相催化剂代替昂贵的均质金属聚吡啶基配合物。这种廉价，可回收的催化剂与SMBR方法的结合，可实现可持续且可扩展的光催化。
• Direct C–F Bond Formation Using Photoredox Catalysis
  作者：Montserrat Rueda-Becerril、Olivier Mahé、Myriam Drouin、Marek B. Majewski、Julian G. West、Michael O. Wolf、Glenn M. Sammis、Jean-François Paquin

  DOI：10.1021/ja412083f

  日期：2014.2.12

  We have developed the first example of a photoredox catalytic method for the formation of carbon-fluorine (C-F) bonds. The mechanism has been studied using transient absorption spectroscopy and involves a key single-electron transfer from the (MLCT)-M-3 (triplet metal-to-ligand charge transfer) state of Ru(bpy)(3)(2+) to Selectfluor. Not only does this represent a new reaction for photoredox catalysis, but the mild reaction conditions and use of visible light also make it a practical improvement over previously developed UV-mediated decarboxylative fluorinations.