2-pyridyl fluoroiodomethyl sulfone | 1415115-02-4

• 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-pyridyl fluoroiodomethyl sulfone
• 英文别名: 2-((Fluoroiodomethyl)sulfonyl)pyridine；2-[fluoro(iodo)methyl]sulfonylpyridine
• CAS: 1415115-02-4
• 化学式: C₆H₅FINO₂S
• 分子量: 301.08
• InChiKey: XXSXBEYUENKPJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 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：
  55.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-碘氰基苯 、 2-pyridyl fluoroiodomethyl sulfone 在 diethylzinc 、 copper(l) iodide 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 以88%的产率得到
  参考文献：
  名称：

  Copper-Mediated Fluoroalkylation of Aryl Iodides Enables Facile Access to Diverse Fluorinated Compounds: The Important Role of the (2-Pyridyl)sulfonyl Group

  摘要：

  The (2-pyridyl)sulfonyl group was found to be a multifunctional group in the preparation of structurally diverse fluorinated products. It not only facilitates the copper-mediated (or catalyzed) cross-coupling reaction between a-fluoro sulfone 4a and aryl iodides, but also enables further transformations of the coupling products 2.

  DOI：

  10.1021/ol3029737
• 作为产物：
  描述：

  氟甲基2-吡啶基砜 在 N-碘代丁二酰亚胺 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以72%的产率得到2-pyridyl fluoroiodomethyl sulfone
  参考文献：
  名称：

  Copper-Mediated Fluoroalkylation of Aryl Iodides Enables Facile Access to Diverse Fluorinated Compounds: The Important Role of the (2-Pyridyl)sulfonyl Group

  摘要：

  The (2-pyridyl)sulfonyl group was found to be a multifunctional group in the preparation of structurally diverse fluorinated products. It not only facilitates the copper-mediated (or catalyzed) cross-coupling reaction between a-fluoro sulfone 4a and aryl iodides, but also enables further transformations of the coupling products 2.

  DOI：

  10.1021/ol3029737

文献信息

• Palladium‐Catalyzed Defluorinative Coupling of Difluoroalkenes and Aryl Boronic Acids for Ketone Synthesis
  作者：Guangwu Sun、Herui Liu、Xiu Wang、Wenbo Zhang、Wenjun Miao、Qinyu Luo、Bing Gao、Jinbo Hu

  DOI：10.1002/anie.202213646

  日期：2023.1.2

  A palladium-catalyzed defluorinative coupling reaction of gem-difluoroalkenes and aryl boronic acids affords ketones with an α-all-carbon quaternary center. The vinyl difluoromethylene motif serves as an in situ carbonyl precursor that is unprecedented in transition-metal-catalyzed coupling reactions. The key difluoroalkyl palladium(II) RCF2−PdII intermediate and related organometallic species were

  钯催化的偕二氟烯烃和芳基硼酸的脱氟偶联反应提供了具有 α-全碳季中心的酮。乙烯基二氟亚甲基基序用作原位羰基前体，这在过渡金属催化的偶联反应中是前所未有的。关键的二氟烷基钯 (II) RCF 2 -Pd II中间体和相关的有机金属物种得到了充分表征。