[Fluoro(iodo)methyl]sulfonylbenzene | 1415115-03-5

• 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: [Fluoro(iodo)methyl]sulfonylbenzene
• 英文别名: [fluoro(iodo)methyl]sulfonylbenzene
• CAS: 1415115-03-5
• 化学式: C₇H₆FIO₂S
• 分子量: 300.092
• InChiKey: WAFQNLGBHDKCTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [Fluoro(iodo)methyl]sulfonylbenzene 、 3-氟苯基硼酸 在 bis(acetylacetonate)nickel(II) 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以81%的产率得到1-[Benzenesulfonyl(fluoro)methyl]-3-fluorobenzene
  参考文献：
  名称：

  镍催化的芳基硼酸单氟甲基化

  摘要：

  芳基硼酸可以在镍催化下被单氟甲基化。他汀类药物依泽替米贝的硼酸化和酰基保护衍生物的单氟甲基化证明了该方法的实用性。机理研究表明，氟甲基参与了Ni I / Ni III催化循环。

  DOI：

  10.1002/anie.201412026
• 作为产物：
  描述：

  氟甲基苯基砜 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74%的产率得到[Fluoro(iodo)methyl]sulfonylbenzene
  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

• Combinatorial Nickel-Catalyzed Monofluoroalkylation of Aryl Boronic Acids with Unactivated Fluoroalkyl Iodides
  作者：Jie Sheng、Hui-Qi Ni、Ge Liu、Yan Li、Xi-Sheng Wang

  DOI：10.1021/acs.orglett.7b02012

  日期：2017.9.1

  A combinatorial nickel-catalyzed cross-coupling between arylboronic acids and unactived 1-fluoro-1-iodoalkanes has been developed, which demonstrated high efficiency, mild conditions, and excellent functional-group compatibility. Readily available nitrogen and phosphine ligands were combined with a nitrogen source, which in situ generated a variety of easily tunable catalysts to promote the fluoroalkylation

  已经开发了芳基硼酸和未反应的1-氟-1-碘代烷烃之间的镍组合催化交叉偶联反应，显示出高效率，温和的条件和出色的官能团相容性。易于获得的氮和膦配体与氮源结合，可就地生成各种易于调节的催化剂，从而在两个偶合伙伴的广泛范围内促进氟烷基化。这种组合催化的新策略为镍催化的交叉偶联反应提供了新的解决方案。
• Copper-Mediated Fluoroalkylation of Aryl Iodides Enables Facile Access to Diverse Fluorinated Compounds: The Important Role of the (2-Pyridyl)sulfonyl Group
  作者：Yanchuan Zhao、Bing Gao、Chuanfa Ni、Jinbo Hu

  DOI：10.1021/ol3029737

  日期：2012.12.7

  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.
• Nickel-Catalyzed Monofluoromethylation of Aryl Boronic Acids
  作者：Yi-Ming Su、Guang-Shou Feng、Zhen-Yu Wang、Quan Lan、Xi-Sheng Wang

  DOI：10.1002/anie.201412026

  日期：2015.5.11

  Aryl boronic acids can be monofluoromethylated under nickel catalysis. The utility of this method is demonstrated by the monofluoromethylation of a borylated and acyl‐protected derivative of the statin drug ezetimibe. Mechanistic investigations indicate that a fluoromethyl radical is involved in the NiI/NiIII catalytic cycle.

  芳基硼酸可以在镍催化下被单氟甲基化。他汀类药物依泽替米贝的硼酸化和酰基保护衍生物的单氟甲基化证明了该方法的实用性。机理研究表明，氟甲基参与了Ni I / Ni III催化循环。