(2,3,4,5,6-pentafluorophenyl)methyl trifluoromethyl sulfone | 405074-85-3

• 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: (2,3,4,5,6-pentafluorophenyl)methyl trifluoromethyl sulfone
• 英文别名: pentafluorobenzyl trifluoromethyl sulfone；pentafluorobenzyl triflate；Benzene, pentafluoro[[(trifluoromethyl)sulfonyl]methyl]-；1,2,3,4,5-pentafluoro-6-(trifluoromethylsulfonylmethyl)benzene
• CAS: 405074-85-3
• 化学式: C₈H₂F₈O₂S
• 分子量: 314.156
• InChiKey: NZYDYOOOKQEJTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2,3,4,5,6-pentafluorophenyl)methyl trifluoromethyl sulfone 在 叔丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 7.33h， 生成 (4-benzyl-2,3,5,6-tetrafluorophenyl)bis(triflyl)methane
  参考文献：
  名称：

  Facile Synthesis of Aryl- and Alkyl-bis(trifluoromethylsulfonyl)methanes

  摘要：

  通过将相应的苄基卤化物与三氟甲烷亚硫酸钠反应，然后再与三氟甲磺酸酐反应，合成了多种芳香基双(三氟甲磺酰)甲烷 (1)。此外，当1中的芳基是五氟苯基时，芳基的亲核性对位取代反应可以通过烷基锂和烷氧化钠实现。这一反应对于设计新型布朗斯特酸具有实用价值。

  DOI：

  10.1246/bcsj.78.1401
• 作为产物：
  描述：

  Langlois reagent 、 α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 丙腈 作用下， 以89%的产率得到(2,3,4,5,6-pentafluorophenyl)methyl trifluoromethyl sulfone
  参考文献：
  名称：

  Facile Synthesis of Aryl- and Alkyl-bis(trifluoromethylsulfonyl)methanes

  摘要：

  通过将相应的苄基卤化物与三氟甲烷亚硫酸钠反应，然后再与三氟甲磺酸酐反应，合成了多种芳香基双(三氟甲磺酰)甲烷 (1)。此外，当1中的芳基是五氟苯基时，芳基的亲核性对位取代反应可以通过烷基锂和烷氧化钠实现。这一反应对于设计新型布朗斯特酸具有实用价值。

  DOI：

  10.1246/bcsj.78.1401

文献信息

• Role of base in palladium-catalyzed arylation of carbanions
  作者：Anton V Mitin、Alexander N Kashin、Irina P Beletskaya

  DOI：10.1016/j.jorganchem.2003.12.039

  日期：2004.3

  proposed a novel mechanism of palladium-catalyzed arylation of CH-acids. The main feature of this mechanism is the accelaration of the reductive elimination due to the deprotonation of the intermediate ArPdL2CHXY. The correlation between the carbanion reactivity and the pKa values for related CH-acids as well as the ligand effect are discussed in the framework of the proposed mechanism.

  某些砜，氰基乙酸酯和丙二腈衍生的碳负离子与芳基溴化物的芳基化反应（使用Pd 2 dba 3 / 3L的催化体系，L = PPh 3，P t Bu 3）以及碳负离子的反应一当量的4-CF 3 C 6 H 4 Pd（PPh 3）2溴已被研究。只要反应混合物中存在比初始碳负离子强的碱，这些反应就可以顺利进行。在没有上述类型的碱的情况下，反应根本不进行。考虑到这一点，我们提出了钯催化CH-酸芳基化的新机制。该机理的主要特征是由于中间ArPdL 2 CHXY的去质子化而加速了还原消除。在所提出的机理的框架内，讨论了碳负离子反应性和相关CH-酸的p K a值之间的相关性以及配体效应。
• Polystyrene-Bound Tetrafluorophenylbis(triflyl)methane as an Organic-Solvent-Swellable and Strong Brønsted Acid Catalyst The authors thank Mr. Shoichi Kondo for the single-crystal X-ray analysis. Sodium triflate was generously donated by Central Glass Co., Ltd., Japan. The authors also acknowledge Dr. Yuko Wasada and Dr. Manabu Kubota for their helpful discussions on the theoretical calculations.
  作者：Kazuaki Ishihara、Aiko Hasegawa、Hisashi Yamamoto

  DOI：10.1002/1521-3773(20011105)40:21<4077::aid-anie4077>3.0.co;2-1

  日期：2001.11.5

  Several advantages over inorganic solid acids such as zeolites and perfluororesinsulfonic acids such as Nafion are offered by the new reusable polystyrene-bound catalyst 1: a broader range of applications, improved yields, improved selectivity, and milder reaction conditions. Tf = F3 CSO2 .
• Palladium-Catalyzed Arylation of Sulfones
  作者：A. V. Mitin、A. N. Kashin、I. P. Beletskaya

  DOI：10.1023/b:rujo.0000044542.70121.04

  日期：2004.6

  A procedure was developed for monoarylation of sulfones with aryl halides in the presence of palladium complexes. Optimal reaction conditions were found, and the scope of application of the proposed procedure was determined. The arylation occurs only with those sulfones which are relatively strong CH acids, the corresponding monoarylated sulfones are formed in moderate to high yields. The arylation of carbanions derived from the sulfones and some other CH acids requires the presence of an additional equivalent of base. The presence of the latter is also necessary in stoichiometric reactions of carbanions with the palladium complex CF3C6H4Pd(PPh3)(2)Br; no reaction occurs in the absence of a base. A new mechanism of arylation was proposed, where the key stage is deprotonation of palladium intermediate ArPdL2CHXY which activates the reductive elimination stage.
• Facile Synthesis of Aryl- and Alkyl-bis(trifluoromethylsulfonyl)methanes
  作者：Aiko Hasegawa、Takuo Ishikawa、Kazuaki Ishihara、Hisashi Yamamoto

  DOI：10.1246/bcsj.78.1401

  日期：2005.8

  Various arylbis(trifluoromethylsulfonyl)methanes (1) have been synthesized by reacting the corresponding benzylic halides with sodium trifluoromethanesulfinate and then with triflic anhydride. In addition, when the aryl group of 1 is a pentafluorophenyl group, the nucleophilic para-substitution of the aryl group with alkyllithiums and sodium alkoxides occurs. This reaction is useful for the design of new Brønsted acids.

  通过将相应的苄基卤化物与三氟甲烷亚硫酸钠反应，然后再与三氟甲磺酸酐反应，合成了多种芳香基双(三氟甲磺酰)甲烷 (1)。此外，当1中的芳基是五氟苯基时，芳基的亲核性对位取代反应可以通过烷基锂和烷氧化钠实现。这一反应对于设计新型布朗斯特酸具有实用价值。

表征谱图