triethyl-(3,4-dimethyl-phenyl)-silane | 18415-16-2

• 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: triethyl-(3,4-dimethyl-phenyl)-silane
• 英文别名: Triaethyl-(3,4-dimethyl-phenyl)-silan；3,4-Dimethylphenyl-triaethylsilan；3.4-Dimethylphenyl-triaethylsilan；(3,4-Dimethylphenyl)-triethylsilane
• CAS: 18415-16-2
• 化学式: C₁₄H₂₄Si
• 分子量: 220.43
• InChiKey: LDYNGWUMLMVIIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 邻二甲苯 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 1,2-二[(2R,5R)-2,5-二异丙基磷杂环戊烷基]乙烷 、 环己烯 作用下， 以 neat (no solvent) 为溶剂， 反应 20.0h， 以77%的产率得到triethyl-(3,4-dimethyl-phenyl)-silane
  参考文献：
  名称：

  Intermolecular C–H Silylation of Arenes and Heteroarenes with HSiEt₃under Operationally Diverse Conditions: Neat/Stoichiometric and Acceptor/Acceptorless

  摘要：

  Efficient protocols for Rh-catalyzed intermolecular C-H silylation of unactivated arenes and heteroarenes are disclosed. The silylations are catalyzed by a Rh-complex (2 mol %) derived in situ from commercially available Rh(nbd)(2)BF4 and (S,S)-i-Pr-BPE (L3) with Et3SiH in the presence of hydrogen acceptor under either neat (excess of arene) or stoichiometric conditions. The regioselectivity is determined mainly by the steric bulk of the substituents and by the electronic effect as an ancillary factor. In addition, our preliminary result shows that the current protocol catalyzes the silylation of arenes in the absence of hydrogen acceptors.

  DOI：

  10.1021/acscatal.5b02806

文献信息

• Intermolecular and Intramolecular, Platinum-Catalyzed, Acceptorless Dehydrogenative Coupling of Hydrosilanes with Aryl and Aliphatic Methyl C−H Bonds
  作者：Naofumi Tsukada、John F. Hartwig

  DOI：10.1021/ja050612p

  日期：2005.4.1

  Intermolecular acceptorless dehydrogenative coupling of silanes with arene C-H bonds and intramolecular coupling of silanes with aryl and alkyl C-H bonds occur in good yield in the presence of 5 mol % of TpMe2PtMe2H (TpMe2 = hydridotris(3,5-dimethylpyrazolyl)borate) and related platinum(IV) complexes. The intermolecular reactions of arenes occurred with both trialkyl and dialkylaryl silanes. Intramolecular reactions of dialkylsilylalkylarenes occurred at aryl C-H bonds, and reactions of tributylsilane or dibutylphenylsilane occurred intramolecularly at the aliphatic, primary C-H bond. The reactions of arenes occurred preferentially at the least sterically hindered C-H bonds and preferentially with more electron-poor arenes. Crossover experiments and the lack of reactivity of the arylsilanes with H2 imply that the dehydrogenative silylation of arenes can be irreversible, even in a closed reaction vessel.
• Toptschiew et al., Doklady Akademii Nauk SSSR, 1958, vol. 118, p. 731,732,734
  作者：Toptschiew et al.

  DOI：——

  日期：——
• Intermolecular C–H Silylation of Arenes and Heteroarenes with HSiEt₃under Operationally Diverse Conditions: Neat/Stoichiometric and Acceptor/Acceptorless
  作者：Kang-sang Lee、Dimitris Katsoulis、Jongwook Choi

  DOI：10.1021/acscatal.5b02806

  日期：2016.3.4

  Efficient protocols for Rh-catalyzed intermolecular C-H silylation of unactivated arenes and heteroarenes are disclosed. The silylations are catalyzed by a Rh-complex (2 mol %) derived in situ from commercially available Rh(nbd)(2)BF4 and (S,S)-i-Pr-BPE (L3) with Et3SiH in the presence of hydrogen acceptor under either neat (excess of arene) or stoichiometric conditions. The regioselectivity is determined mainly by the steric bulk of the substituents and by the electronic effect as an ancillary factor. In addition, our preliminary result shows that the current protocol catalyzes the silylation of arenes in the absence of hydrogen acceptors.