1,3-dipropargylimidazolium bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-dipropargylimidazolium bromide
• 英文别名: 1,3-Diprop-2-ynyl-1h-imidazol-3-ium bromide；1,3-bis(prop-2-ynyl)imidazol-1-ium;bromide
• 化学式: Br*C₉H₉N₂
• 分子量: 225.088
• InChiKey: JTVQVSKQWRLATR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.95
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-dipropargylimidazolium bromide 在 tetra-n-butylammonium acetylacetonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成
  参考文献：
  名称：

  Synthesis of Propargyl-Functionalized NHC Gold Complexes

  摘要：

  A series of propargyl functionalized N-heterocyclic carbene gold(I) complexes have been synthesized from the corresponding imidazolium salts with tetrabutylammonium acetylacetonate in the presence of a gold(I) precursor in a one-pot reaction. Several complexes of different stoichiometries are described: [AuBr(NHC)], [Au(NHC)(2)]Br and [Au(C6F5)(NHC)], and many of these have been characterized by X-ray diffraction studies. Aurophilic interactions are present in the compounds bearing less sterically hindered carbenes, and secondary interactions such as hydrogen bonds, pi-pi stacking, or weak contacts of the gold center with the carbon of the propargyl unit have also been found. These complexes possess a high degree of water solubility, which makes them potentially useful for the synthesis of biologically active compounds or as gold catalysts in water. Activation of the propargyl unit in [AuBr(NHC)] complexes leads to the formation of interesting trimers with bridging bidentate C boolean AND C alkynyl-carbene ligands.

  DOI：

  10.1021/acs.organomet.7b00012
• 作为产物：
  描述：

  3-溴丙炔 、 三甲基硅咪唑 以 甲苯 为溶剂， 反应 24.0h， 以94%的产率得到1,3-dipropargylimidazolium bromide
  参考文献：
  名称：

  由PEG标记的咪唑鎓盐稳定的金纳米颗粒，可作为可再生催化剂用于炔丙基胺的合成和γ-链烷酸的环异构化

  摘要：

  我们报告了含有三唑连接基的聚乙二醇化咪唑鎓盐（溴化物和四氟硼酸盐）和三咪唑鎓盐（溴化物）的合成，以及它们作为稳定剂用于制备水溶性金纳米颗粒的方法，该方法是通过用硼氢化钠还原四氯金酸来制备的。纳米材料已被表征。X射线光电子能谱（XPS）表明存在Au（I）和Au（0）物质，氧化形式在衍生自溴化三咪唑鎓的纳米材料中更丰富。这些金纳米颗粒的催化活性已在A 3中证明。羰基化合物，末端炔烃和胺之间的偶合，得到炔丙基胺，以及将γ-炔酸环化为烯醇内酯。源自PEG标记的三咪唑鎓溴化物的纳米材料提供了最佳性能，并且利用其溶解度特性已在两个反应（多达四个和六个运行）中进行了回收。

  DOI：

  10.1039/d0nj00284d

文献信息

• Palladium(II) Complexes of a Neutral CCC-Tris(N-heterocyclic carbene) Pincer Ligand: Synthesis and Catalytic Applications
  作者：David Rendón-Nava、Deyanira Angeles-Beltrán、Arnold L. Rheingold、Daniel Mendoza-Espinosa

  DOI：10.1021/acs.organomet.1c00324

  日期：2021.7.12

  tris-azolium precursor 1 with palladium acetate under thermal conditions provided a CCC-pincer palladium(II) complex (2) bearing three NHCs (one imidazolylidene and two triazolylidenes) and one iodide ligand. Further treatment of complex 2 with an excess of AgSbF6 generates tris(carbene) dicationic palladium complex 3 in which the iodine ligands are exchanged with SbF6 anions and the metal center is stabilized

  在热条件下用乙酸钯处理三唑鎓前体1提供了带有三个 NHC（一个咪唑亚基和两个三唑基亚基）和一个碘化物配体的 CCC-钳状钯 (II) 复合物 ( 2 )。用过量的 AgSbF 6进一步处理配合物2生成三（卡宾）双阳离子钯配合物3，其中碘配体与 SbF 6阴离子交换，金属中心由一个乙腈配体稳定。配合物2和3在几个交叉偶联反应中进行了测试，显示在低催化剂负载和温和反应条件下的高转化率。此外，复合体2和3在末端炔烃的氢化硅烷化中表现良好，对E-异构体具有良好的选择性。
• Nonpolar phase-soluble methathesis catalysts
  申请人：Bergbreiter David E.

  公开号：US20090203860A1

  公开（公告）日：2009-08-13

  One embodiment of the invention provides polyisobutylene (PIB) oligomers that are end-functionalized with ruthenium (Ru) catalysts. Such nonpolar catalysts can be dissolved in nonpolar solvents such as heptane, or any other nonpolar solvent that is otherwise not latently biphasic (i.e., if two or more solvent components are present, they remain miscible with each other throughout the entire reaction process, from the addition of substrate through to the removal of product). Substrate that is dissolved in the nonpolar solvent with the catalyst is converted into product. The lower solubility of the product in the nonpolar solvent renders it easily removable, either by extraction with a more polar solvent or by applying physical means in cases where the product precipitates from the nonpolar solvent. In this manner the catalysts are recycled; since the catalysts remain in the nonpolar solvent, a new reaction can be initiated simply by dissolving fresh substrate into the nonpolar solvent.

  本发明的一个实施例提供了末端功能化与钌（Ru）催化剂的聚异丁烯（PIB）寡聚体。这种非极性催化剂可以溶解在非极性溶剂中，如庚烷，或者任何其他否则不是潜在两相的非极性溶剂（即，如果存在两种或更多的溶剂成分，则它们在整个反应过程中保持互溶，从底物的加入到产品的去除）。溶解在带有催化剂的非极性溶剂中的底物会转化为产物。产物在非极性溶剂中的较低溶解度使其易于去除，可以通过用更极性的溶剂萃取或者在产物从非极性溶剂中沉淀的情况下应用物理手段来实现。通过这种方式，催化剂可以循环利用；由于催化剂保留在非极性溶剂中，只需将新的底物溶解到非极性溶剂中，就可以简单地启动新的反应。
• Electrochemical Synthesis of Gold‐<i>N</i>‐Heterocyclic Carbene Complexes**
  作者：Thomas P. Nicholls、Zhongfan Jia、Justin M. Chalker

  DOI：10.1002/chem.202303161

  日期：2024.1.8

  An electrochemical synthesis of gold(I)-N-heterocyclic carbene (Au-NHC) complexes has been developed in which the only by-product is hydrogen gas. This enables the clean Au-NHC complexes to be transferred directly to subsequent catalytic reactions without extra work-up. This telescoped methodology has been showcased for several mononuclear and dinuclear Au-NHC complexes in a catalytic vinylcyclopropanation

  开发了金（I） -N-杂环卡宾（Au-NHC）配合物的电化学合成方法，其中唯一的副产物是氢气。这使得干净的 Au-NHC 配合物能够直接转移到后续催化反应中，无需额外的后处理。这种伸缩方法已在催化乙烯基环丙烷化反应中展示了几种单核和双核 Au-NHC 配合物，可实现高产率并证明程序简单。
• Convenient Transfer Semihydrogenation Methodology for Alkynes Using a Pd^II-NHC Precatalyst
  作者：Ruben M. Drost、Tessel Bouwens、Nicolaas P. van Leest、Bas de Bruin、Cornelis J. Elsevier

  DOI：10.1021/cs4011502

  日期：2014.5.2

  A convenient and easy-to-use protocol for the Z-selective transfer semihydrogenation of alkynes was developed, using ammonium formate as the hydrogen source and the easily prepared and commercially available, highly stable complex PdC1(eta(3)-C3H5)(IMes) (1) as the (pre)catalyst. Combined with triphenyl posphine as an additional ligand, this system provides a robust catalytic synthetic method that shows little to no over-reduction or isomerization after full substrate conversion. The system allows the direct use of solvents and reagents, as received from the supplier without drying or purification, thus providing a practical method for semihydrogenation of a broad range of alkynes. The mechanism behind these high and enhanced selectivities was determined through a set of kinetic experiments.
• Synthesis and Application of N-Heterocyclic Carbene–Palladium Ligands with Glycerol Dendrons for the Suzuki–Miyaura Cross-Coupling in Water
  作者：Rainer Haag、Maike Lukowiak、Markus Meise

  DOI：10.1055/s-0034-1378533

  日期：——