4-methyl-2-(perfluorophenyl)thiophene

• 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: 4-methyl-2-(perfluorophenyl)thiophene
• 英文别名: 4-Methyl-2-(2,3,4,5,6-pentafluorophenyl)thiophene；4-methyl-2-(2,3,4,5,6-pentafluorophenyl)thiophene
• 化学式: C₁₁H₅F₅S
• 分子量: 264.219
• InChiKey: SLOBIPXQSFNHCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲基噻吩 、 五氟苯 在 palladium diacetate 、 溶剂黄146 、 silver carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以47%的产率得到4-methyl-2-(perfluorophenyl)thiophene
  参考文献：
  名称：

  Pd-Catalyzed Oxidative Cross-Coupling of Perfluoroarenes with Aromatic Heterocycles

  摘要：

  A straightforward and practical method for direct Pd(OAc)(2)-catalyzed oxidative cross-coupling of electron-deficient perfluoroarenes with aromatic heterocycles has been developed. Because of its low catalyst loading (2.5 mol %), high reaction efficiency, good chemo- and regioselectivity, and excellent functional-group compatibility, this protocol provides a useful and operationally simple access to perfluoroarene thiophene structures of interest in functional materials for electronic devices.

  DOI：

  10.1021/ja106046p

文献信息

• Perfluorophenylation of aromatic and heteroaromatic compounds with pentafluorobenzenesulfonyl chloride catalyzed by a ruthenium (II) phosphine complex
  作者：Nobumasa Kamigata、Manabu Yoshikawa、Toshio Shimizu

  DOI：10.1016/s0022-1139(97)00120-6

  日期：1998.1

  The reactions of pentafluorobenzenesulfonyl chloride with benzene and thiophene derivatives in the presence of a ruthenium(II) catalyst proceeded at 240°C, with extrusion of sulfur dioxide and hydrogen chloride, to give the corresponding perfluorophenylated compounds.

  在钌（II）催化剂存在下，五氟苯磺酰氯与苯和噻吩衍生物的反应在240℃下进行，同时挤出二氧化硫和氯化氢，得到相应的全氟苯基化的化合物。
• Pd-Catalyzed Oxidative Cross-Coupling of Perfluoroarenes with Aromatic Heterocycles
  作者：Chun-Yang He、Shilu Fan、Xingang Zhang

  DOI：10.1021/ja106046p

  日期：2010.9.22

  A straightforward and practical method for direct Pd(OAc)(2)-catalyzed oxidative cross-coupling of electron-deficient perfluoroarenes with aromatic heterocycles has been developed. Because of its low catalyst loading (2.5 mol %), high reaction efficiency, good chemo- and regioselectivity, and excellent functional-group compatibility, this protocol provides a useful and operationally simple access to perfluoroarene thiophene structures of interest in functional materials for electronic devices.