1,4-di(2,6-diisopropylphenyl)-3-methyl-H-1,2,3-triazolium iodide | 1443747-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-di(2,6-diisopropylphenyl)-3-methyl-H-1,2,3-triazolium iodide
• 英文别名: 1,4-di(2,6-diisopropylphenyl)-1,2,3-triazolium iodide
• CAS: 1443747-04-3
• 化学式: C₂₇H₃₈N₃*I
• 分子量: 531.523
• InChiKey: PFQIEHNPJOWRNE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  copper(l) iodide 、 1,4-di(2,6-diisopropylphenyl)-3-methyl-H-1,2,3-triazolium iodide 在 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到(iodido){1,4-di(2,6-diisopropylphenyl)-3-methyl-1,2,3-triazol-5-ylidene}copper(I)
  参考文献：
  名称：

  Copper(I) Complexes of Mesoionic Carbene: Structural Characterization and Catalytic Hydrosilylation Reactions

  摘要：

  100℃,100℃,10“C,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃

  DOI：

  10.3390/molecules20047379
• 作为产物：
  描述：

  2,6-diisopropyl-1-azidobenzene 在 吡啶 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 144.0h， 生成 1,4-di(2,6-diisopropylphenyl)-3-methyl-H-1,2,3-triazolium iodide
  参考文献：
  名称：

  单和双介离子卡宾硼烷：作为还原剂的合成、结构和效用

  摘要：

  1,2,3-三唑-5-亚基类型的介离子卡宾 (MIC) 是目前有机金属化学中流行的配体。它们在主族化学中的应用相当有限。在这篇文章中，我们介绍了基于三唑基的 MIC 的单和双 MIC-硼烷。该合成涉及相应三唑鎓盐的原位去质子化以及它们与硼烷反应形成所需化合物。尽管该反应路线对于衍生自三唑的 1,4-区域异构体的所有三唑鎓盐均运行良好，但对于衍生自 1,5-取代三唑的亚甲基桥连双三唑鎓盐，我们观察到双-三唑鎓和具有新的 NB 键的三唑硼烷的形成。所有化合物均通过多核 NMR 光谱、质谱、和单晶X射线衍射。此外，MIC-硼烷用作还原剂，用于将醛的 C=O 还原为相应的醇。

  DOI：

  10.1002/ejic.202100273

文献信息

• Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by PEPPSI-Type 1,4-Di(2,6-diisopropylphenyl)-1,2,3-triazol-5-ylidene (<i>tz</i>IPr) Palladium Complex
  作者：Jie Huang、Jong-Tai Hong、Soon Hyeok Hong

  DOI：10.1002/ejoc.201201075

  日期：2012.10.11

  A 1,4-di(2,6-diisopropylphenyl)-1,2,3-triazol-5-ylidene (tzIPr)-based PEPPSI-type palladium complex was developed as an excellent precatalyst for the Suzuki–Miyaura cross-coupling reaction. The complex showed high activity under mild conditions for the cross-coupling reactions between various types of aryl chlorides and aryl boronic acids regardless of the steric and electronic nature of the substrates

  开发了一种基于 1,4-二(2,6-二异丙基苯基)-1,2,3-三唑-5-亚基 (tzIPr) 的 PEPPSI 型钯配合物作为 Suzuki-Miyaura 交叉偶联反应的优异预催化剂. 无论底物的空间和电子性质如何，该配合物在各种类型的芳基氯化物和芳基硼​​酸之间的交叉偶联反应中都显示出温和条件下的高活性。
• Palladium(ii)-Acetylacetonato Complexes with Mesoionic Carbenes: Synthesis, Structures and Their Application in the Suzuki-Miyaura Cross Coupling Reaction
  作者：Lara Hettmanczyk、Bianca Schmid、Stephan Hohloch、Biprajit Sarkar

  DOI：10.3390/molecules21111561

  日期：——

  from the corresponding triazolium iodides and palladium(ii) acetylacetonate is described herein. All complexes were characterized by 1H- and 13C-NMR spectroscopy and high resolution mass spectrometry. Additionally, two of the complexes were characterized by single crystal X-ray crystallography confirming a square-planar coordination geometry of the palladium(ii) center. A delocalized bonding situation

  已经合成并表征了一系列带有介离子卡宾 (MIC) 的新型钯 (ii) 乙酰丙酮络合物。(MIC)Pd(acac)I 型配合物的合成 (MIC = 1-mesityl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (1), 1,4-( 2,4,6-甲基)-苯基-3-甲基-1,2,3-三唑-5-亚基(2), 1,4-(2,6-二异丙基)-苯基-3-甲基-1,本文描述了从相应的碘化三唑鎓和乙酰丙酮钯 (ii) 开始直接金属化的 2,3-三唑-5-亚基 (3)；acac = 乙酰丙酮)。所有配合物均通过 1H-和 13C-NMR 光谱和高分辨率质谱进行表征。此外，其中两个配合物通过单晶 X 射线晶体学表征，证实了钯 (ii) 中心的方形平面配位几何形状。分别在三唑基环内和 acac 配体中观察到离域键合情况。发现配合物 2 是芳基溴化物或芳基氯化物与苯基硼酸之间
• Mono- and Digold(I) Complexes with Mesoionic Carbenes: Structural Characterization and Use in Catalytic Silver-Free Oxazoline Formation
  作者：Lara Hettmanczyk、Dennis Schulze、Lisa Suntrup、Biprajit Sarkar

  DOI：10.1021/acs.organomet.6b00675

  日期：2016.11.28

  Triazolylidenes are a prominent class of mesoionic carbenes that have found use as supporting ligands in homogeneous catalysis in recent years. We present here the syntheses of three new mononuclear gold(I) chlorido and two new dinuclear gold(I) chlorido complexes. The ligands in the aforementioned complexes are derived from either the corresponding monotriazolium or the bitriazolium salts. All complexes have been characterized by H-1 and C-13H-1} NMR spectroscopy, mass spectrometry, and single-crystal X-ray diffraction studies. Structural characterization delivers a delocalized bonding situation within the triazolylidene ligands and a linear coordination at the gold(I) centers. The gold(I) centers in all cases are bound to one triazolylidene-C donor and a chlorido ligand. Additionally, for the digold(I) complexes large Au-Au distances were observed, ruling out the existence of aurophilic interactions in these digold complexes in the solid state. All of the gold(I) complexes were tested as (pre)catalysts for the cyclization reaction of propargylic amides to form oxazolines. We show here that the steric bulk of the substituents on the triazolylidene ligands plays a decisive role in the catalytic efficiency of the gold(I) complexes. Copper(II) triflate is. shown as a viable alternative to silver(I) salts as an additive for the oxazoline formation. Mechanistic studies show the detection of a gold(I) triazolylidene vinyl complex as an intermediate in the catalytic synthesis of oxazoline with these complexes. These results thus establish copper(II) triflate as an alternative to silver(I) salts as an additive in gold(I) triazolylidene catalysis. Furthermore, it also shows that steric tuning of triazolylidene ligands can indeed be utilized for increasing the catalytic efficiency of the corresponding complexes.