bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfoxide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfoxide
• 英文别名: 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-Heptadecafluoro-10-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfinyl)decane；1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfinyl)decane
• 化学式: C₂₀H₈F₃₄OS
• 分子量: 942.295
• InChiKey: VCIWRZKCHYKDEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  36

反应信息

• 作为产物：
  描述：

  1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-十七氟-10-碘庚烷 在 过氧乙酸 、 三乙基硼氢化锂 、 sulfur 作用下， 以 四氢呋喃 、 氯仿 、 溶剂黄146 为溶剂， 反应 3.25h， 生成 bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfoxide
  参考文献：
  名称：

  Syntheses, oxidations, and palladium complexes of fluorous dialkyl sulfides: new precursors to highly active catalysts for the Suzuki coupling

  摘要：

  Reactions of Rf(8)(CH2)(n)I(R-f8=CF3(CF2)(7)) with Li2S give the fluorous dialkyl sulfides (R-f8(CH2)(n))(2)S (n=2, 1, 71%; 3, 2, 67%) as low melting white solids that are soluble in most fluorous and organic solvents. Reactions of 1 and 2 with CH3CO3H yield the corresponding sulfoxides (R-f8(CH2)(n))(2)S=O (85; 80%), which are soluble in CF3C6F5 at room temperature, but insoluble in most other solvents. At higher temperatures, solubilities can become appreciable. Reactions of 1 and 2 with Na2PdCl4 (ca. 0.5 equiv.) give palladium complexes [(R-f8(CH2)(n))(2)S](2)PdCl2 (5, 94%; 6, 95%), which are soluble in only a limited range of fluorinated solvents at room temperature. The CF3C6F11/toluene partition coefficients of 1 and 2 are 98.7:1.3 and 96.6:3.4 (24degreesC). The Suzuki coupling of aryl bromides and PhB(OH)(2) to biaryls is catalyzed by 5 and 6 (0.02 mol%) in CF3C6F11/DMF/H2O in the presence of K3PO4, generally at room temperature. Turnover numbers of 4500-5000 are easily achieved. However, activities decrease under fluorous biphase recycling conditions, and implications for the nature of the catalytically active species are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00275-2

文献信息

• Syntheses, oxidations, and palladium complexes of fluorous dialkyl sulfides: new precursors to highly active catalysts for the Suzuki coupling
  作者：Christian Rocaboy、J.A Gladysz

  DOI：10.1016/s0040-4020(02)00275-2

  日期：2002.5

  Reactions of Rf(8)(CH2)(n)I(R-f8=CF3(CF2)(7)) with Li2S give the fluorous dialkyl sulfides (R-f8(CH2)(n))(2)S (n=2, 1, 71%; 3, 2, 67%) as low melting white solids that are soluble in most fluorous and organic solvents. Reactions of 1 and 2 with CH3CO3H yield the corresponding sulfoxides (R-f8(CH2)(n))(2)S=O (85; 80%), which are soluble in CF3C6F5 at room temperature, but insoluble in most other solvents. At higher temperatures, solubilities can become appreciable. Reactions of 1 and 2 with Na2PdCl4 (ca. 0.5 equiv.) give palladium complexes [(R-f8(CH2)(n))(2)S](2)PdCl2 (5, 94%; 6, 95%), which are soluble in only a limited range of fluorinated solvents at room temperature. The CF3C6F11/toluene partition coefficients of 1 and 2 are 98.7:1.3 and 96.6:3.4 (24degreesC). The Suzuki coupling of aryl bromides and PhB(OH)(2) to biaryls is catalyzed by 5 and 6 (0.02 mol%) in CF3C6F11/DMF/H2O in the presence of K3PO4, generally at room temperature. Turnover numbers of 4500-5000 are easily achieved. However, activities decrease under fluorous biphase recycling conditions, and implications for the nature of the catalytically active species are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.