Perfluorobenzyl triflate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Perfluorobenzyl triflate
• 英文别名: [Difluoro-(2,3,4,5,6-pentafluorophenyl)methyl] trifluoromethanesulfonate
• 化学式: C₈F₁₀O₃S
• 分子量: 366.136
• InChiKey: RDDUQVPGGCUDDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Perfluorobenzyl triflate 在 potassium iodide 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 1.0h， 以92%的产率得到七氟苄碘
  参考文献：
  名称：

  A new route to polyfluorinated trifluoromethanesulfonates. Synthesis of perfluoroallyl and perfluorobenzyl triflates

  摘要：

  Polyfluoroalkyl trifluoromethanesulfonates (triflates) can be prepared in good to excellent yields by the reaction of halofluoroalkanes such as CFC-11, CFC-113 and CFC-112 with boron triflate at 20-25 degrees C. Hexafluoropropene (HFP) is more active and reacts with B(OSO2CF3)(3) even at 0 degrees C to give perfluoroallyl triflate in 68% yield. Octafluorotoluene, 1,1,2-trichloro-3,3,3-trifluoroprop-1-ene and hexafluoro-2,3-dichloro-but-2-ene also produce the corresponding triflates in 30-60% yields on reaction with boron triflate.

  DOI：

  10.1016/0022-1139(94)03210-q
• 作为产物：
  描述：

  boron triflate 、 八氟甲苯 反应 4.0h， 以30%的产率得到Perfluorobenzyl triflate
  参考文献：
  名称：

  A new route to polyfluorinated trifluoromethanesulfonates. Synthesis of perfluoroallyl and perfluorobenzyl triflates

  摘要：

  Polyfluoroalkyl trifluoromethanesulfonates (triflates) can be prepared in good to excellent yields by the reaction of halofluoroalkanes such as CFC-11, CFC-113 and CFC-112 with boron triflate at 20-25 degrees C. Hexafluoropropene (HFP) is more active and reacts with B(OSO2CF3)(3) even at 0 degrees C to give perfluoroallyl triflate in 68% yield. Octafluorotoluene, 1,1,2-trichloro-3,3,3-trifluoroprop-1-ene and hexafluoro-2,3-dichloro-but-2-ene also produce the corresponding triflates in 30-60% yields on reaction with boron triflate.

  DOI：

  10.1016/0022-1139(94)03210-q

文献信息

• Silicon Tetrakis(trifluoromethanesulfonate): A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid
  作者：André Hermannsdorfer、Matthias Driess

  DOI：10.1002/anie.202103414

  日期：2021.6.7

  leads to [L2Si(OTf)4] complexes (L=isocyanide, thioether and carbonyl compounds) with retention of all Si−OTf bonds. In contrast, it can cleave C−X bonds (X=F, Cl) of hard organic Lewis bases with a high tendency to form SiX4 (X=F, Cl) after halide/triflate exchange. Most notable, Si(OTf)4 allows a gentle oxydefluorination of mono- and bis(trifluoromethyl)benzenes, resulting in the formation of the corresponding

  据报道，原始硅四（三氟甲磺酸）Si(OTf) 4的简单合成和分离是第一种适用于软和硬路易斯碱的中性硅基路易斯超强酸。其 OTf 基团具有双重功能：它们是优异的离去基团，并调节对软路易斯碱和硬路易斯碱的反应程度。暴露于软路易斯供体时，Si(OTf) 4产生[L 2 Si(OTf) 4 ]配合物（L=异氰化物、硫醚和羰基化合物），并保留所有Si−OTf键。相反，它可以裂解硬有机路易斯碱的CX键（X = F，Cl），并且在卤化物/三氟甲磺酸酯交换后很容易形成SiX 4 （X = F，Cl）。最值得注意的是，Si(OTf) 4允许单（三氟甲基）苯和双（三氟甲基）苯发生温和的氧化脱氟反应，从而形成相应的苯甲酰鎓物种，并通过弱配位的[Si(OTf) 6 ]二价阴离子进行稳定。
• A new route to polyfluorinated trifluoromethanesulfonates. Synthesis of perfluoroallyl and perfluorobenzyl triflates
  作者：V.A. Petrov

  DOI：10.1016/0022-1139(94)03210-q

  日期：1995.7

  Polyfluoroalkyl trifluoromethanesulfonates (triflates) can be prepared in good to excellent yields by the reaction of halofluoroalkanes such as CFC-11, CFC-113 and CFC-112 with boron triflate at 20-25 degrees C. Hexafluoropropene (HFP) is more active and reacts with B(OSO2CF3)(3) even at 0 degrees C to give perfluoroallyl triflate in 68% yield. Octafluorotoluene, 1,1,2-trichloro-3,3,3-trifluoroprop-1-ene and hexafluoro-2,3-dichloro-but-2-ene also produce the corresponding triflates in 30-60% yields on reaction with boron triflate.