3-butyl-1-methyl-1H-benzo[d]imidazol-3-ium iodide | 108410-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-butyl-1-methyl-1H-benzo[d]imidazol-3-ium iodide
• 英文别名: 1-butyl-3-methyl-1H-benzimidazol-3-ium iodide；1-butyl-3-methylbenzimidazolium iodide
• CAS: 108410-41-9
• 化学式: C₁₂H₁₇N₂*I
• 分子量: 316.185
• InChiKey: JPGYPFMKMUVYEM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl azide 、 3-butyl-1-methyl-1H-benzo[d]imidazol-3-ium iodide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以84%的产率得到(E)-1-butyl-3-methyl-2-((E)-(4-nitrophenyl)triaz-2-en-1-ylidene)-2,3-dihydro-1H-benzo[d]imidazole
  参考文献：
  名称：

  Push-Pull Triazenes Derived from 1-(Benzylideneamino)- and 1-(Sulfonimido)-azolylidenes

  摘要：

  In-situ-generated neutral 1-(benzylideneamino)- and novel anionic 1-(sulfonimido)-azolylidenes react with organic azides to afford diverse classes of push-pull triazenes and triazene salts. The scope of the heterocyclic core and substituents at the N1 and N3 positions of NHC precursors together with the thermal properties of resulting compounds were examined.

  DOI：

  10.1021/jo302697q
• 作为产物：
  描述：

  bis(1-butyl-3-methyl-1,3-dihydro-2H-benzimidazol-2-ylidene)diiodonickel(II) 在 水 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以63%的产率得到3-butyl-1-methyl-1H-benzo[d]imidazol-3-ium iodide
  参考文献：
  名称：

  Facile Hydrolysis of Nickel(II) Complexes with N-Heterocyclic Carbene Ligands

  摘要：

  Metal complexes with N-heterocyclic carbene ligands (NHC) are ubiquitously used in catalysis, where the stability of the metal-ligand framework is a key issue. Our study shows that Ni-NHC complexes may undergo facile decomposition due to the presence of water in organic solvents (hydrolysis). The ability to hydrolyze Ni(NHC)(2)X-2 complexes decreases in the order of NHC = 1,2,4-triazolium > benzimidazolium approximate to imidazolium. Depending on the ligand and substituents, the half reaction time of the complex decomposition may change from several minutes to hours. The nature of the halogen is also an important factor, and the ability for decomposition of the studied complexes decreases in the order of Cl > Br > I. NMR and MS monitoring revealed that Ni-NHC complexes in the presence of water undergo hydrolysis with Ni-C-carbene bond cleavage, affording the corresponding N,N'-dialkylated azolium salts and nickel(II) hydroxide. These findings are of great importance for designing efficient and recyclable catalytic systems, because trace water is a common contaminant in routine synthetic applications.

  DOI：

  10.1021/acs.organomet.5b00856

文献信息

• Cu-catalyzed controllable C–H mono-/di-/triarylations of imidazolium salts for ionic functional materials
  作者：Shiqing Li、Junbin Tang、Yinsong Zhao、Ruyong Jiang、Tianbao Wang、Ge Gao、Jingsong You

  DOI：10.1039/c7cc01076a

  日期：——

  The first Cu-catalyzed direct C-H mono-, di- and triarylations of imidazolium salts with aryl iodides/bromides are reported.

  据报道，咪唑鎓盐与芳基碘化物/溴化物的第一个Cu催化的直接CH直接单，二和三芳基化反应。
• Ni(<scp>ii</scp>)-catalyzed C–H hydroarylation of diarylacetylenes with imidazolium salts
  作者：Tianbao Wang、Xuesong Zheng、Qinze Zheng、Fulin Zhou、Linhua Wang、Ge Gao

  DOI：10.1039/d1cc07309e

  日期：——

  A simple Ni(II)-catalyzed C–H hydroarylation of diarylacetylenes with imidazolium salts without adding any ligand was developed. It provides a facile and efficient access to (E)-2-(1,2-diarylvinyl)imidazolium salts. The preliminary results indicate a rare nonredox catalytic cycle of Ni(II), complementary to the common redox catalytic cycle starting from Ni(0).

  开发了一种简单的 Ni( II ) 催化的二芳基乙炔与咪唑盐的 C-H 加氢芳基化，无需添加任何配体。它提供了一种简便有效的获得 ( E )-2-(1,2-二芳基乙烯基)咪唑盐的途径。初步结果表明 Ni( II ) 的罕见非氧化还原催化循环与从 Ni(0) 开始的常见氧化还原催化循环互补。
• Revealing the unusual role of bases in activation/deactivation of catalytic systems: O–NHC coupling in M/NHC catalysis
  作者：Victor M. Chernyshev、Oleg V. Khazipov、Maxim A. Shevchenko、Andrey Yu. Chernenko、Alexander V. Astakhov、Dmitry B. Eremin、Dmitry V. Pasyukov、Alexey S. Kashin、Valentine P. Ananikov

  DOI：10.1039/c8sc01353e

  日期：——

  intramolecular reducing agents for the transformation of M(II) into “ligandless” M(0) species. This demonstrates that the disclosed base-mediated O–NHC coupling reaction is integrated into the catalytic M/NHC systems and can define the mechanism of catalysis (molecular M/NHC vs. “NHC-free” cocktail-type catalysis). A proposed mechanism of the revealed transformation includes NHC-OR reductive elimination, as

  金属（M）与N-杂环卡宾（NHC）配体的络合物通常会在明显影响性能的氧碱的存在下催化许多反应。人们普遍认为，底物激活（例如铃木交叉偶联中的金属转移）或HX捕获（例如，在各种C–C和C–杂原子耦合，Heck反应，C–H功能化中）都需要碱，杂环化等）。这项研究提供了对M（II）/ NHC（M = Pd，Pt，Ni）配合物在溶液中的行为的见解，该配合物在常规参与催化的碱（KOH，NaOH，t- BuOK，Cs 2 CO 3，K）的作用下2一氧化碳3，等等）。公开了在典型的碱介导的M / NHC催化的反应条件下M（ II）/ NHC络合物的先前未解决的转化。在催化中广泛使用的Pd（ II）和Pt（ II）配合物通过O–NHC偶联机理与碱反应生成M（0）物种和2（5）-氧代取代的唑。Ni（NHC） 2 X 2络合物在氢氧化钾水溶液存在下水解，并经过相同的O–NHC偶联，在t的作用下得到偶氮酮和金属镍