1H-Imidazolium,1-[2-(diphenylphosphino)ethyl]-3-[(3-methoxyphenyl)methyl]-, chloride | 823803-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1H-Imidazolium,1-[2-(diphenylphosphino)ethyl]-3-[(3-methoxyphenyl)methyl]-, chloride
• 英文别名: 3-(2-diphenylphosphanylethyl)-1-(3-methoxybenzyl)-3H-imidazol-1-ium chloride
• CAS: 823803-23-2
• 化学式: C₂₅H₂₆N₂OP*Cl
• 分子量: 436.921
• InChiKey: TWNVFAWOJMYMAH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  18.04
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1H-Imidazolium,1-[2-(diphenylphosphino)ethyl]-3-[(3-methoxyphenyl)methyl]-, chloride 、 palladium dichloride 在 sodium acetate 作用下， 以 二甲基亚砜 为溶剂， 以49%的产率得到(1-(2-diphenylphosphanylethyl)-3-(3-methoxybenzyl)imidazolin-2,2'-diylidene)palladium dichloride
  参考文献：
  名称：

  A convenient synthesis of phosphine-functionalized N-heterocyclic carbene ligand precursors, structural characterization of their palladium complexes and catalytic application in Suzuki coupling reaction

  摘要：

  A series of imidazolium chlorides as ligand precursors, (LHCl)-H-. (L=(1-R)-(3-diphenylphosphanylethyl)-imidazol-2-ylidene; R = aryl, benzyl, naphthylmethyl), for the phosphine-functionalized N-heterocyclic carbene (NHC), L, were prepared by a convenient synthetic procedure of reacting 1,2-dichloroethane with appropriate N-substituted imidazoles to give (beta-chloroethyl)imidazolium chlorides, which were subsequently reacted with HPPh2 producing (LHCl)-H-. in good yield. Palladium complexes of L, PdLCl2 (4), were prepared by a one pot reaction of PdCl2, sodium acetate, and (LHCl)-H-. in DMSO. Complexes 4b (R = naphthylmethyl) and 4e (R = m-methoxybenzyl) were characterized by X-ray crystallography. Catalytic studies have shown that the palladium complexes are efficient in Suzuki coupling reactions of aryl bromides with phenylboronic acid. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2004.06.025

文献信息

• Well-defined palladium(0) complexes bearing N-heterocyclic carbene and phosphine moieties: efficient catalytic applications in the Mizoroki–Heck reaction and direct C–H functionalization
  作者：Jhen-Yi Lee、Jiun-Shian Shen、Ru-Jiun Tzeng、I-Chen Lu、Jenn-Huei Lii、Ching-Han Hu、Hon Man Lee

  DOI：10.1039/c6dt01323f

  日期：——

  Two series of well-defined palladium(0) complexes with phosphine-functionalized N-heterocyclic carbene ligands were prepared. These complexes featured six- and seven-membered chelate rings in the two series. Among the seven-membered chelate complexes, those featuring the PCy2 moiety exhibited observable fluxional behavior on the NMR time scale, corresponding to the interchange between two sets of conformations

  制备了两个系列的具有膦官能化的N-杂环卡宾配体的明确定义的钯（0）配合物。这些配合物在两个系列中具有六元和七元螯合环。在七元螯合物中，具有PCy 2的螯合物在NMR时间尺度上，该部分显示出可观察到的通量行为，对应于两组构象之间的互换。通过单晶X射线衍射研究已成功地对大多数这些新颖的复合物进行了结构表征。测试了这两个系列的钯（0）配合物在两种机理上不同的反应中的潜在催化应用，即Mizoroki-Heck偶联反应和直接的C-H功能化反应。发现六元螯合物中的一种是介导芳基氯和烯烃之间的偶联反应的有效预催化剂。钯（0）配合物也可以有效地用于芳基溴化物与1,2-二甲基咪唑的直接CH功能化反应中。