(E)-dimethyl[4-(2-triethylsilanylvinyl)phenyl]amine | 866364-01-4

• 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: (E)-dimethyl[4-(2-triethylsilanylvinyl)phenyl]amine
• 英文别名: N,N-dimethyl-4-(E-2-(triethylsilyl)vinyl)aniline；N,N-dimethyl-4-[(E)-2-triethylsilylethenyl]aniline
• CAS: 866364-01-4
• 化学式: C₁₆H₂₇NSi
• 分子量: 261.483
• InChiKey: ZIBCIHXVVINJCZ-BUHFOSPRSA-N

物化性质

• 沸点：
  343.2±35.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基乙烯基硅烷 、 4-溴-N,N-二甲基苯胺 在 bis(η3-allyl-μ-chloropalladium(II)) sodium acetate 、 顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以76%的产率得到(E)-dimethyl[4-(2-triethylsilanylvinyl)phenyl]amine
  参考文献：
  名称：

  Selective synthesis of (E)-triethyl(2-arylethenyl)silane derivatives by reaction of aryl bromides with triethyl vinylsilane catalysed by a palladium–tetraphosphine complex

  摘要：

  Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/0.5[PdCI(C3H5)](2) system catalyses the Heck reaction of vinylsilane derivatives with a range of aryl bromides with high ratio substrate/catalyst in good yields. The formation of mixtures of styrene, (E)-triethyl(2-arylethenyl)sitane and triethyl(1-arylethenyl)silane derivatives was observed in some cases. Very high selectivities (up to 100%) in favour of the formation of (E)-triethyl(2-arylethenyl)silane derivatives were obtained in the presence of sodium acetate as base. With other bases such as potassium carbonate, the formation of large amounts of styrene derivatives was observed. The reaction tolerates several functions such as fluoro, trifluoromethyl, methoxy, dimethylamino, acetyl, formyl, benzoyl, carboxylate, nitro or nitrile. Moreover, turnover numbers up to 10,000 can be obtained for this reaction. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.05.014

文献信息

• Palladium(II) Complexes of a Neutral CCC-Tris(N-heterocyclic carbene) Pincer Ligand: Synthesis and Catalytic Applications
  作者：David Rendón-Nava、Deyanira Angeles-Beltrán、Arnold L. Rheingold、Daniel Mendoza-Espinosa

  DOI：10.1021/acs.organomet.1c00324

  日期：2021.7.12

  tris-azolium precursor 1 with palladium acetate under thermal conditions provided a CCC-pincer palladium(II) complex (2) bearing three NHCs (one imidazolylidene and two triazolylidenes) and one iodide ligand. Further treatment of complex 2 with an excess of AgSbF6 generates tris(carbene) dicationic palladium complex 3 in which the iodine ligands are exchanged with SbF6 anions and the metal center is stabilized

  在热条件下用乙酸钯处理三唑鎓前体1提供了带有三个 NHC（一个咪唑亚基和两个三唑基亚基）和一个碘化物配体的 CCC-钳状钯 (II) 复合物 ( 2 )。用过量的 AgSbF 6进一步处理配合物2生成三（卡宾）双阳离子钯配合物3，其中碘配体与 SbF 6阴离子交换，金属中心由一个乙腈配体稳定。配合物2和3在几个交叉偶联反应中进行了测试，显示在低催化剂负载和温和反应条件下的高转化率。此外，复合体2和3在末端炔烃的氢化硅烷化中表现良好，对E-异构体具有良好的选择性。
• Regioselective hydrosilylation of terminal alkynes using pentamethylcyclopentadienyl iridium(III) metallacycle catalysts
  作者：Yann Corre、Christophe Werlé、Lydia Brelot-Karmazin、Jean-Pierre Djukic、Francine Agbossou-Niedercorn、Christophe Michon

  DOI：10.1016/j.molcata.2016.07.014

  日期：2016.11

  adienyl iridium(III) metallacycles catalyse the hydrosilylation of alkynes using triethylsilane and no additive. The reactions proceed rapidly and efficiently at low catalyst loadings and under mild reaction conditions. If catalyses starting from terminal alkynes lead selectively to (Z)-alkenylsilanes in high yields, reactions are less efficient and selective starting from internal alkynes due to steric

  摘要 五甲基环戊二烯基铱 (III) 金属环在不使用添加剂的情况下使用三乙基硅烷催化炔烃的氢化硅烷化。反应在低催化剂负载和温和的反应条件下快速有效地进行。如果从末端炔烃开始的催化剂以高产率选择性地导致 (Z)-烯基硅烷，则由于空间位阻和可能形成异喹啉鎓盐，从内部炔烃开始的反应效率和选择性较低。质谱法强调了多达两个连续的 1,2-炔烃插入催化剂铱-碳键。
• Rhodium(I) Complexes Bearing Hydroxyl‐Functionalized 1,2,3‐Triazolylidenes and Their Catalytic Application
  作者：Agustín A. de la Fuente‐Olvera、Franciso J. Ruiz‐Mendoza、José M. Vásquez‐Pérez、Myriam Meléndez‐Rodríguez、Alejandro Álvarez‐Hernández、Verónica Salazar‐Pereda、Daniel Mendoza‐Espinosa

  DOI：10.1002/ejic.202200401

  日期：2022.10.26

  We report the synthesis and full characterization of a novel series rhodium(I) complexes (3 a–c) supported by hydroxyl-functionalized 1,2,3-triazolylidenes. Their application as catalysts in the 1,4-addition of boronic acid to 2-cyclohexenone and the hydrosilylation of terminal alkynes is described.

  我们报告了由羟基官能化的 1,2,3-三唑基支持的新型系列铑 (I) 配合物 ( 3 a-c )的合成和完整表征。描述了它们作为催化剂在硼酸与 2-环己烯酮的 1,4-加成和末端炔烃的氢化硅烷化中的应用。
• Rhodium-Catalyzed Alkenylation of Nitriles via Silicon-Assisted C−CN Bond Cleavage
  作者：Yusuke Kita、Mamoru Tobisu、Naoto Chatani

  DOI：10.1021/ol100481h

  日期：2010.4.16

  Rhodium-catalyzed Mizoroki-Heck type reaction of nitriles via the cleavage of C-C bonds is described. Orthogonal and iterative functionalizations of arenes were also demonstrated by combining the present and conventional halide-based cross-coupling reactions.
• Selective synthesis of (E)-triethyl(2-arylethenyl)silane derivatives by reaction of aryl bromides with triethyl vinylsilane catalysed by a palladium–tetraphosphine complex
  作者：Ahmed Battace、Touriya Zair、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.jorganchem.2005.05.014

  日期：2005.8

  Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/0.5[PdCI(C3H5)](2) system catalyses the Heck reaction of vinylsilane derivatives with a range of aryl bromides with high ratio substrate/catalyst in good yields. The formation of mixtures of styrene, (E)-triethyl(2-arylethenyl)sitane and triethyl(1-arylethenyl)silane derivatives was observed in some cases. Very high selectivities (up to 100%) in favour of the formation of (E)-triethyl(2-arylethenyl)silane derivatives were obtained in the presence of sodium acetate as base. With other bases such as potassium carbonate, the formation of large amounts of styrene derivatives was observed. The reaction tolerates several functions such as fluoro, trifluoromethyl, methoxy, dimethylamino, acetyl, formyl, benzoyl, carboxylate, nitro or nitrile. Moreover, turnover numbers up to 10,000 can be obtained for this reaction. (c) 2005 Elsevier B.V. All rights reserved.