NHC | 1482496-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: NHC
• CAS: 1482496-31-0
• 化学式: C₂₁H₂₆N₄
• 分子量: 334.464
• InChiKey: SACZHNCOUZETMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  22.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  NHC 、 palladium diacetate 以 四氢呋喃 为溶剂， 以48%的产率得到(1-tert-butyl-4-{2-[(N,N-dimethylamino)methyl]phenyl}-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide)palladium(II) diacetate
  参考文献：
  名称：

  Palladium(II) Complexes of 1,2,4-Triazole-Based N-Heterocyclic Carbenes: Synthesis, Structure, and Catalytic Activity

  摘要：

  Six palladium(II) complexes bearing three different triazole-based N-heterocyclic carbene (NHC) ligands, [1-tert-butyl-4-{2-[(N,N-dimethylamino)methyl]phenyl}-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide, 1-tert-butyl-4-(2-methoxyphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide, and 1-tert-butyl-4-(4-methylphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide], were synthesized and fully characterized. NMR spectroscopy and X-ray diffraction analysis revealed that the amino-group-substituted NHC ligand is coordinated in bidentate fashion, forming a monocarbene chelate complex with an additional intramolecular Pd <- N bond with the nitrogen donor atom. The 4-methylphenyl- and 2-methoxyphenyl-substituted NHC ligands coordinate as C-monodentate donors, forming simple biscarbene Pd(II) complexes. The evaluation of the catalytic performance in the Suzuki-Miyaura cross-coupling reaction revealed very promising performance of the intramolecularly coordinated monocarbene complexes under relatively mild conditions even in direct comparison with the commercially available PEPPSI catalyst. In contrast, the biscarbene complexes proved inactive in this catalytic process. According to theoretical calculations (EDA and NOCV analysis), functionalization of the 1,2,4-triazole-based NHC with the 2-[(N,N-dimethylamino)methyl]phenyl group has a significant effect on the stability of the NHC metal bond.

  DOI：

  10.1021/om500342z
• 作为产物：
  描述：

  1-(tert-Butyl)-4-(2-((dimethylamino)methyl)phenyl)-3-phenyl-4H-1,2,4-triazol-1-ium Perchlorate 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以85%的产率得到NHC
  参考文献：
  名称：

  Amino Group Functionalized N-Heterocyclic 1,2,4-Triazole-Derived Carbenes: Structural Diversity of Rhodium(I) Complexes

  摘要：

  The synthesis of the amino group functionalized NHC precursor 1-tert-butyl-4-(2-((dimethylamino)methyl)-phenyl)-3-phenyl-4H-1,2,4-triazol-1-ium perchlorate has been developed. The generation and bonding properties of the NHC ligand have been evaluated in reactions toward three Rh(I) complexes - [Rh(COD)Cl](2), [Rh(cyclooctene)(2)Cl](2), and [Rh(ethylene)(2)Cl](2) respectively. For the first complex, [(NHC)RhCl(COD)], the coordination of the dangling amino group was not observed because of the fully occupied coordination neighborhood of the Rh atom. On the other hand, in the case of [(NHC)RhCl(ethylene)], [(NHC)RhCl(cyclooctene)], [(NHC)Rh(COD)](+)[BF4](-), and [(NHC)RhCl(CO)] a strong intramolecular coordination of the amino nitrogen atom was revealed, thus forming the unusual seven-membered diazametallacycle. All of the products of these reactions were characterized in solution by NMR spectroscopy as well as in the solid state by X-ray diffraction analysis.

  DOI：

  10.1021/om400912s