(2-methoxyphenyl)triphenylsilane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-methoxyphenyl)triphenylsilane
• 英文别名: (2-Methoxyphenyl)-triphenylsilane；(2-methoxyphenyl)-triphenylsilane
• 化学式: C₂₅H₂₂OSi
• 分子量: 366.535
• InChiKey: QVLHWCOVPFGDEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-碘苯甲醚 、 三苯基硅烷 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate potassium phosphate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 96.0h， 以99%的产率得到(2-methoxyphenyl)triphenylsilane
  参考文献：
  名称：

  Direct and Selective Arylation of Tertiary Silanes with Rhodium Catalyst

  摘要：

  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.

  DOI：

  10.1021/jo8008148

文献信息

• Dehydrocoupling of alkoxyarenes with aromatic hydrosilanes catalyzed by scandium aminobenzyl complexes
  作者：A. I. Babkin、A. A. Kissel、A. M. Ob’edkov、A. A. Trifonov

  DOI：10.1007/s11172-022-3614-z

  日期：2022.9

  Scandium tris(o-aminobenzyl) complex Sc(o-CH2C6H4NMe2)3 (1) and its cationic derivative [Sc(o-CH2C6H4NMe2)2][B(C6F5)4] (2) catalyze the dehydrocoupling of alkoxyarenes with various aromatic hydrosilanes in toluene at 90 °C to give C-H silylation products in 15–89% yields (24 h). The product yield depends on the nature and the ratio of the substrates, and the new carbon-silicon bond is formed only in

  三( o-氨基苄基)钪配合物Sc( o - CH 2 C 6 H 4 NMe 2 ) 3 ( 1 )及其阳离子衍生物[Sc( o - CH 2 C 6 H 4 NMe 2 ) 2 ][B(C 6 F 5 ) 4 ] ( 2) 在 90 °C 的甲苯中催化烷氧基芳烃与各种芳族氢硅烷的脱氢偶联，以 15-89% 的收率 (24 小时) 得到 CH 甲硅烷基化产物。产物收率取决于底物的性质和比例，新的碳-硅键仅在芳环中烷氧基取代基的邻位形成。阳离子络合物2被证明是一种比中性络合物1更具活性的脱氢偶联催化剂，并提供 55-89%对15-45% 的底物转化率。根据 NMR 光谱数据，配合物1在催化反应中与两种底物发生反应。1与苯甲醚的反应伴随邻位后者的金属化反应得到配合物 ( o -CH 2 C 6 H 4 NMe 2 ) 2 Sc( o -C 6 H 4 OMe) ( 4 )，而与 PhSiH 3反应得到氢化物
• Rhodium-catalyzed silylation of ortho-functionalized aryl halides with hydrosilanes
  作者：Yoshinori Yamanoi、Hiroshi Nishihara

  DOI：10.1016/j.tetlet.2006.08.001

  日期：2006.10

  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.
• 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.