(4-chlorophenyl)(2,3,5,6-tetrafluorophenyl)sulfane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4-chlorophenyl)(2,3,5,6-tetrafluorophenyl)sulfane
• 英文别名: 1-(p-Chlor-phenylmercapto)-2,3,5,6-tetrafluor-benzol；3-(4-Chlorophenyl)sulfanyl-1,2,4,5-tetrafluorobenzene
• 化学式: C₁₂H₅ClF₄S
• 分子量: 292.684
• InChiKey: CULZXNLGNCYAPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,4'-二氯二苯二硫醚 、 (4-chlorophenyl)(2,3,5,6-tetrafluorophenyl)sulfane 在 1,10-菲罗啉 、 copper(I) bromide 、 lithium tert-butoxide 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 以86%的产率得到1,4-bis(4-chlorophenylthio)-2,3,5,6-tetrafluorobenzene
  参考文献：
  名称：

  通过 CH 和 CF 键活化铜催化五氟苯与二芳基二硫化物或芳基硫醇的直接硫醇化

  摘要：

  使用 CuBr 作为催化剂，tBuOLi 或 tBuOK 作为碱在 DMSO 中，在 60 °C 和 O2 气氛下，Cu 催化二芳基二硫化物或芳基硫醇与五氟苯的交叉偶联反应。通过 C-H 键和 C-F 键活化，以中等至良好的产率获得了相应的双芳基硫醇化产物。当1,10-菲咯啉·H2O和DDQ加入到上述体系中时，可以以中等产率分离出有/没有双芳基硫代产物的单芳基硫代产物。给出了这些转换的合理机制。因此，它代表了一种通过 C-H 键和 C-F 键活化合成多氟二芳基硫化物和多氟三芳基二硫化物的方法。

  DOI：

  10.1002/ejoc.201101676
• 作为产物：
  描述：

  S-acetyl-4-chlorothiophenol 、 五氟苯 在 potassium carbonate 、 L-脯氨酸 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到(4-chlorophenyl)(2,3,5,6-tetrafluorophenyl)sulfane
  参考文献：
  名称：

  Regioselective C–S bond formation accomplished by copper-catalyzed regioselective C–F substitution of perfluoroarenes with aryl thioacetates or benzyl thioacetate

  摘要：

  Practical and straightforward method for regioselective C-S bond formation accomplished by copper-catalyzed regioselective C-F substitution of electron-deficient perfluoroarenes with aryl thioacetates or benzyl thioacetate has been developed. Because of its high reaction efficiency, good chemoselectivity and regioselectivity, and excellent functional-group compatibility, this protocol provides a useful and operationally simple access to polyfluoroaryl thioethers used for drugs and material chemistry. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.091

文献信息

• Synthesis of polyfluorinated aromatic ethers and thioethers by synergistic cleavage of C-B bond and C-F bond of B(C6F5)3
  作者：Cui-Cui Ma、Xing-Xing Zhu、Li Liu、Jian-Jun Dai、Jun Xu、Hua-Jian Xu

  DOI：10.1016/j.tetlet.2021.153387

  日期：2021.10

  A concise and efficient method for the synthesis of polyfluorinated aromatic ethers and thioethers by synergistic cleavage of C-B bond and C-F bond of B(C6F5)3 is reported. The reaction could proceed smoothly with excellent functional-group compatibility. In addition, the transformation represents the first general application of B(C6F5)3 as reaction partners in cross-coupling reaction.

  报道了一种通过协同裂解 B(C 6 F 5 ) 3的 CB 键和 CF 键合成多氟芳族醚和硫醚的简洁有效的方法。反应可以顺利进行，具有良好的官能团相容性。此外，该转变代表了 B(C 6 F 5 ) 3作为交叉偶联反应中的反应伙伴的首次普遍应用。
• Regioselective C-S Bond Formation Accomplished by Regioselective C-F Substitution of Polyfluoroarenes with Substituted Thiophenols
  作者：Qizhong Zhou、Bin Zhang、Haining Gu、Aiguo Zhong、Tieqi Du、Qiong Zhou、Yuyuan Ye、Zhengneng Jin、Huajiang Jiang、Rener Chen

  DOI：10.2174/157017812800167493

  日期：2012.3.1

  The nucleophilic aromatic substitution reaction of pentafluorobenzene, methyl 2,3,4,5-tetrafluorobenzoic acid ester and 1,2,4,5-tetrafluorobenzene with substituted thiophenols showed good regioselectivity while pentafluorobenzene gave high yields. The computational results suggest that the specificity difference between polyfluorobenzenes originates from their electronic properties.

  五氟苯，2,3,4,5-四氟苯甲酸甲酯和1,2,4,5-四氟苯与取代的苯酚的亲核芳族取代反应显示出良好的区域选择性，而五氟苯的收率很高。计算结果表明，多氟苯之间的特异性差异源自其电子性能。
• Regioselective C–S bond formation accomplished by copper-catalyzed regioselective C–F substitution of perfluoroarenes with aryl thioacetates or benzyl thioacetate
  作者：Qizhong Zhou、Bin Zhang、Tieqi Du、Haining Gu、Huajiang Jiang、Rener Chen

  DOI：10.1016/j.tet.2012.03.091

  日期：2012.6

  Practical and straightforward method for regioselective C-S bond formation accomplished by copper-catalyzed regioselective C-F substitution of electron-deficient perfluoroarenes with aryl thioacetates or benzyl thioacetate has been developed. Because of its high reaction efficiency, good chemoselectivity and regioselectivity, and excellent functional-group compatibility, this protocol provides a useful and operationally simple access to polyfluoroaryl thioethers used for drugs and material chemistry. (C) 2012 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Direct Thiolation of Pentafluorobenzene with Diaryl Disulfides or Aryl Thiols by C-H and C-F Bond Activation
  作者：Chuanming Yu、Cuiling Zhang、Xiangjun Shi

  DOI：10.1002/ejoc.201101676

  日期：2012.4

  A Cu-catalyzed cross-coupling reaction of diaryl disulfides or aryl thiols with pentafluorobenzene using CuBr as the catalyst, tBuOLi or tBuOK as the base in DMSO at 60 °C under an O2 atmosphere was investigated. The corresponding bisarylthiolation products were obtained in moderate to good yields by C–H bond and C–F bond activation. When 1,10-phenanthroline·H2O and DDQ were added to the above system

  使用 CuBr 作为催化剂，tBuOLi 或 tBuOK 作为碱在 DMSO 中，在 60 °C 和 O2 气氛下，Cu 催化二芳基二硫化物或芳基硫醇与五氟苯的交叉偶联反应。通过 C-H 键和 C-F 键活化，以中等至良好的产率获得了相应的双芳基硫醇化产物。当1,10-菲咯啉·H2O和DDQ加入到上述体系中时，可以以中等产率分离出有/没有双芳基硫代产物的单芳基硫代产物。给出了这些转换的合理机制。因此，它代表了一种通过 C-H 键和 C-F 键活化合成多氟二芳基硫化物和多氟三芳基二硫化物的方法。