ethyl 4-[(trimethylsilyl)methyl]benzoate

• 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: ethyl 4-[(trimethylsilyl)methyl]benzoate
• 英文别名: Ethyl 4-(trimethylsilylmethyl)benzoate
• 化学式: C₁₃H₂₀O₂Si
• 分子量: 236.386
• InChiKey: RBGMRWRICGTDFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  碘甲基三甲基硅烷 、 对碘苯甲酸乙酯 在 1,1,3,3-四甲基脲 、 锌 、 1,1'-双(二苯基膦)二茂铁 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 反应 36.0h， 以87%的产率得到ethyl 4-[(trimethylsilyl)methyl]benzoate
  参考文献：
  名称：

  Synthesis of Functionalized Benzylsilanes from Arylzinc Compounds and (Iodomethyl)trimethylsilane by Means of a Novel Rh Catalysis

  摘要：

  [GRAPHICS]The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH2I was examined in which the Rh complex, generated in situ from [RhCl(1,5-cyclooctadiene)](2) and 1,1'-bis(diphenylphosphino)ferrocene, exhibited excellent catalytic activity for the production of various functionalized benzylsilanes in good yields. From P-31 NMR studies of various solutions containing several of the reaction components, confirmation of the rapid and quantitative transfer of aryl groups from ArZnI to the Rh complex to form arylrhodium species was ascertained. A catalytic cycle, commencing with the transmetalation, was thus proposed for the reaction.

  DOI：

  10.1021/jo0520994

文献信息

• Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands
  作者：Giuseppe Dilauro、Claudia S. Azzollini、Paola Vitale、Antonio Salomone、Filippo M. Perna、Vito Capriati

  DOI：10.1002/anie.202101571

  日期：2021.5.3

  Pd‐catalyzed Negishi cross‐coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)‐C(sp2) and C(sp2)‐C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature

  当在NaCl或可生物降解的氯化胆碱/尿素低共熔混合物存在下使用大量水作为反应介质时，有机锌化合物与（杂）芳基溴化物之间的钯催化Negishi交叉偶联反应已有报道。C（sp 3）‐C（sp 2）和C（sp 2）‐C（sp 2）已经发现，在空气中的温和条件下（室温或60°C），并与质子分解竞争时，偶联能以高化学选择性平稳地进行。其他好处包括非常短的反应时间（20 s），良好至优异的产率（高达98％），广泛的底物范围以及对各种官能团的耐受性。所提出的新颖协议是可扩展的，并且该方法的实用性通过催化剂和低共熔混合物或水的容易再循环而进一步突出。
• Synthesis of Functionalized Benzylsilanes from Arylzinc Compounds and (Iodomethyl)trimethylsilane by Means of a Novel Rh Catalysis
  作者：Hideki Takahashi、Kabir M. Hossain、Yasushi Nishihara、Takanori Shibata、Kentaro Takagi

  DOI：10.1021/jo0520994

  日期：2006.1.1

  [GRAPHICS]The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH2I was examined in which the Rh complex, generated in situ from [RhCl(1,5-cyclooctadiene)](2) and 1,1'-bis(diphenylphosphino)ferrocene, exhibited excellent catalytic activity for the production of various functionalized benzylsilanes in good yields. From P-31 NMR studies of various solutions containing several of the reaction components, confirmation of the rapid and quantitative transfer of aryl groups from ArZnI to the Rh complex to form arylrhodium species was ascertained. A catalytic cycle, commencing with the transmetalation, was thus proposed for the reaction.