1-methyl-2-diphenylphosphino-3-methylimidazolium triflate | 1379677-77-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-methyl-2-diphenylphosphino-3-methylimidazolium triflate
• 英文别名: 1,3-dimethyl-2-(diphenylphosphino)imidazolium triflate
• CAS: 1379677-77-6
• 化学式: CF₃O₃S*C₁₇H₁₈N₂P
• 分子量: 430.387
• InChiKey: AJSIRORTPOOHNE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.01
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-methyl-2-diphenylphosphino-3-methylimidazolium triflate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 氘代苯 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  1,3-Dimethyl-4-(diphenylphosphino)imidazolium Triflate: A Functionalized Ionic Liquid with Ambivalent Coordination Capability

  摘要：

  Simply using 1-methylimidazole as the starting material, the functionalized ionic liquid 1,3-dimethyl-4-(diphenylphosphino)imidazolium triflate ([3]OTf) has been prepared, from which the corresponding 4-phosphino-substituted N-heterocyclic carbene 4 was generated. The coordination capability of 3 and 4 toward a variety of transition-metal centers has been studied, as well as their electron-donor character through an evaluation of the TEP parameter. 3 behaves as a cationic phosphine ligand, whereas 4 shows a strong preference to coordinate to transition metals through the carbene carbon atom, leading to the obtention of mononuclear complexes with a free phosphine arm which act as metalloligands, allowing for the modular formation of homo- and heterodinuclear transition-metal complexes.

  DOI：

  10.1021/acs.organomet.5b00722
• 作为产物：
  描述：

  ClPPh2 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 1-methyl-2-diphenylphosphino-3-methylimidazolium triflate
  参考文献：
  名称：

  4,5-二膦基取代的咪唑鎓盐：模块化合成二膦-NHC杂金属配合物的结构单元

  摘要：

  融合在同一分子中！N-杂环卡宾和二膦生成并用于各种目标杂金属配合物的模块合成。实验方法涉及简单地从1-甲基咪唑开始形成独特的4,5-双（二苯基膦基）-1,3-二甲基咪唑鎓盐（参见方案; M 1 = Cr，Mn; M 2 = Au，Rh ，Pd； LiHMDS ＝ LiN（SiMe 3）2）。

  DOI：

  10.1002/chem.201200031

文献信息

• The ionic mononuclear and trinuclear Au(I)-complexes ligated by phosphine-functionalized ionic liquids: Synthesis, characterization, and catalysis to hydration of phenylacetylene
  作者：Xuezhu Wang、Yongyong Wang、Jing Zhang、Xiaoli Zhao、Ye Liu

  DOI：10.1016/j.jorganchem.2014.04.005

  日期：2014.7

  A series of ionic Au(I)-complexes ligated by the phosphine-functionalized ionic liquids were synthesized and characterized, which are composed of the Au(I)-complex cation and the counteranion of OTf , AuCl4, or PF6-, respectively. The single crystal X-ray diffraction analyses show that the Au(I)-centered vector in 1A, 1B, 2A, 3A, and 4A all possess the slightly twisted linear geometry, and in each individual the Au(I)-center is coordinated by one chlorine and one imidazolium-based phosphine. The aggregation of 1B in acetone can lead to the formation of the trinuclear Au(I)-complex of 1C due to the aurophilic Au(I)-Au(I) interaction, the electrostatic attraction, and the steric preference. When these ionic Au-complexes were employed as precatalysts for hydration of phenylacetylene in aqueous-methanol media, the reaction proceeded selectively according to Markovnikov's rule with moderate to high yields of acetophenone. The highest activities were achieved over 2A with hydrophobic PF6- as the counteranion and the trinuclear 1C under mild conditions (75 degrees C, 2 h), in conjunction with the additive of proton acid H2SO4. The ion-pair effect on the catalytic performance of the corresponding Au(I)-complexes, coming from the phosphine-ligated cations and the counteranions, were investigated. (C) 2014 Elsevier B. V. All rights reserved.