(2-methylsulfanylphenyl)triethylsilane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-methylsulfanylphenyl)triethylsilane
• 英文别名: Triethyl-(2-methylsulfanylphenyl)silane
• 化学式: C₁₃H₂₂SSi
• 分子量: 238.469
• InChiKey: QOWFTVYTCDTUDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 2-碘茴香硫醚 在 反式-双(三苯基膦)合氯化羰基铑(Ⅰ) potassium phosphate 作用下， 以 various solvent(s) 为溶剂， 反应 168.0h， 以99%的产率得到(2-methylsulfanylphenyl)triethylsilane
  参考文献：
  名称：

  Rhodium-catalyzed silylation of ortho-functionalized aryl halides with hydrosilanes

  摘要：

  The silylation of ortho-functionalized aryl iodide with trialkylsilanes in the presence of RhCl(CO)(PPh3)(2) or [Rh(cod)(2)]BF4 and K3PO4 provides the corresponding arylalkylsilane in good to high yield. This catalytic system showed a dramatically different activity when Pd(t-Bu3P)(2) was used as a catalyst. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.001

文献信息

• Direct and Selective Arylation of Tertiary Silanes with Rhodium Catalyst
  作者：Yoshinori Yamanoi、Hiroshi Nishihara

  DOI：10.1021/jo8008148

  日期：2008.9.1

  We have developed a convenient and efficient approach to the arylation of tertiary silanes under mild conditions. A variety of arylsilanes were synthesized in a one-step process with good to excellent yields in the presence of a rhodium catalyst with a base. The reaction was highly solvent dependent, and amides were the most effective of the various solvents used. This common catalyst system is highly tolerant of the various sensitive functional groups on the substrates, which might be difficult to extract by other methods. The rhodium-promoted silylation of aryl halides with electron-donating groups occurred more efficiently than the silylation of aryl halides substituted with electron-withdrawing groups. Heteroaromatic halides were also found to be readily silylated with tertiary silanes. The successful application of this reaction to the synthesis of a TAC-101 analogue, which is a trialkylsilyl-containing synthetic retinoid benzoic acid derivative with selective binding affinity for retinoic acid receptor-alpha, is also described.