(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolyl-2-ylidene)Pd(N,N-dimethylbenzylamine(-1H)-κ2N,C)Cl

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolyl-2-ylidene)Pd(N,N-dimethylbenzylamine(-1H)-κ2N,C)Cl
• 化学式: C₃₀H₃₈ClN₃Pd
• 分子量: 582.525
• InChiKey: INIRZZMDBRAOLK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-二甲基苄胺 、 palladium dichloride 、 N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate 在 Cs₂CO₃ 作用下， 以 乙腈 为溶剂， 以98%的产率得到(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolyl-2-ylidene)Pd(N,N-dimethylbenzylamine(-1H)-κ2N,C)Cl
  参考文献：
  名称：

  Practical One-Pot, Three-Component Synthesis of N-Heterocyclic Carbene (NHC) Ligated Palladacycles Derived from N,N-Dimethylbenzylamine

  摘要：

  Further explorations of the catalytic potential of N-heterocyclic carbene (NHC) ligated palladacycles as catalysts for Pd-mediated transformations have been hampered by the lack of general and practical methods for their synthesis. In this work, we describe a novel, practical approach to NHC-ligated palladacycles by a three-component, one-pot reaction of imidazoliurn salts, PdCl2, and N,N-dimethylbenzylamine in the presence of excess K2CO3 under reflux in reagent-grade acetonitrile in air. 1,3-Diarylimidazolium salts afford the corresponding NHC-Pd(dmba)Cl (dmba = N,N-dimethylbenzylamine-k(2) N,C) complexes in > 80% yield. The conversion of 1,3-diaryl-4,5-dihydroimidazolium and 1,3-dialkylimidazolium or benzimidazolium salts requires the use of stronger base (Cs2CO3) and/or higher temperature (100 degrees C). The Pd-bound chloride anion can be exchanged with silver salts or sodium salts. The NHC-palladacycle adducts have been characterized by single-crystal X-ray crystallography.

  DOI：

  10.1021/om8008475

文献信息

• Practical One-Pot, Three-Component Synthesis of N-Heterocyclic Carbene (NHC) Ligated Palladacycles Derived from <i>N</i>,<i>N</i>-Dimethylbenzylamine
  作者：Eric Assen B. Kantchev、Jackie Y. Ying

  DOI：10.1021/om8008475

  日期：2009.1.12

  Further explorations of the catalytic potential of N-heterocyclic carbene (NHC) ligated palladacycles as catalysts for Pd-mediated transformations have been hampered by the lack of general and practical methods for their synthesis. In this work, we describe a novel, practical approach to NHC-ligated palladacycles by a three-component, one-pot reaction of imidazoliurn salts, PdCl2, and N,N-dimethylbenzylamine in the presence of excess K2CO3 under reflux in reagent-grade acetonitrile in air. 1,3-Diarylimidazolium salts afford the corresponding NHC-Pd(dmba)Cl (dmba = N,N-dimethylbenzylamine-k(2) N,C) complexes in > 80% yield. The conversion of 1,3-diaryl-4,5-dihydroimidazolium and 1,3-dialkylimidazolium or benzimidazolium salts requires the use of stronger base (Cs2CO3) and/or higher temperature (100 degrees C). The Pd-bound chloride anion can be exchanged with silver salts or sodium salts. The NHC-palladacycle adducts have been characterized by single-crystal X-ray crystallography.