trimethyl[(2-diphenylthiophosphinyl)ferrocenylmethyl]ammonium iodide | 854497-26-0

• 英文名称: trimethyl[(2-diphenylthiophosphinyl)ferrocenylmethyl]ammonium iodide
• 英文别名: 2-(diphenylthiophosphinoferrocenyl)trimethylammonium iodide
• CAS: 854497-26-0
• 化学式: C₂₆H₂₉FeNPS*I
• 分子量: 601.314
• InChiKey: DBLCIANFHOJYMN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  trimethyl[(2-diphenylthiophosphinyl)ferrocenylmethyl]ammonium iodide 、 三甲氧基磷 以 xylene 为溶剂， 以20%的产率得到dimethyl [2-(diphenylthiophosphinyl)ferrocenyl]methyl phosphonate
  参考文献：
  名称：

  Labrue, Francis; Pons, Benedicte; Ricard, Louis, Journal of Organometallic Chemistry, 2005, vol. 690, p. 2285 - 2290

  摘要：

  DOI：
• 作为产物：
  描述：

  [2-(N,N-dimethylaminomethyl)ferrocenyl]diphenylphosphine sulfide 、 碘甲烷 以 乙醚 为溶剂， 以95%的产率得到trimethyl[(2-diphenylthiophosphinyl)ferrocenylmethyl]ammonium iodide
  参考文献：
  名称：

  Synthesis and catalytic applications of new chiral ferrocenyl P,O ligands

  摘要：

  A new method to synthesize both enantiomers of 2-diphenylphosphino-ferrocenecarboxaldehyde with the phosphine group protected as a thiophosphine group was developed. These aldehydes react with 1 2 or 1,3 diols to give, in good yields, new chiral phosphine-acetals. For unsymmetrical (R)-1,3-butanediol, the new asymmetrical acetalic carbon is asymmetric and its configuration was completely controlled by the chirality of the diol. These new P,O ligands were tested in the palladium-catalyzed asymmetric allylic substitution of 1,3-diphenylprop-2-enylacetate. Good yields and enantioselectivities up to 77% were observed. The catalytic performances of two diastereoisomeric ligands with opposite configurations in planar chirality only proved to be significantly different, showing a strong influence of both planar and central chiralities. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.11.053

文献信息

• Phosphine/N-heterocyclic carbene palladium complex for Suzuki-Miyaura cross-coupling reactions: The role of water on activity
  作者：Youssra Doria Lahneche、Abdelhak Lachguar、Clément Mouton、Jean-Claude Daran、Eric Manoury、Rinaldo Poli、Meriem Benslimane、Agnès Labande、Eric Deydier

  DOI：10.1016/j.ica.2019.04.021

  日期：2019.6

  rac-6 in the Suzuki-Miyaura coupling of aryl bromides with arylboronic acids. The catalyst proved also to be active for the coupling of more challenging, bulky substrates such as 1-bromo-2-methylnaphthalene and naphthylboronic acid at relatively mild temperatures (40–70 °C) and low loadings (0.1–0.5 mol%). Experiments carried out with various amounts of water highlighted the role of water on both activity

  摘要合成了一种新的双齿二茂铁基二膦/ N-杂环卡宾（NHC）钯配合物rac-6，该配合物带有官能化的悬垂臂，可以进一步接枝到固体表面上，并具有良好的收率。通过在单晶上的X射线衍射获得了配体rac-4-BF4和复合rac-6的分子结构。动力学研究表明，rac-6在芳基溴化物与芳基硼酸的Suzuki-Miyaura偶联中具有良好的活性和稳定性。在相对温和的温度（40–70°C）和低负荷（0.1–0.5 mol％）的条件下，该催化剂还被证明可用于偶联更具挑战性的大体积底物，例如1-溴-2-甲基萘和萘基硼酸。用各种量的水进行的实验突出了水在活性和机理上的作用。