1,5,6-Trimethyl-2-(4-methylphenyl)benzimidazole | 1612157-13-7

• 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: 1,5,6-Trimethyl-2-(4-methylphenyl)benzimidazole
• CAS: 1612157-13-7
• 化学式: C₁₇H₁₈N₂
• 分子量: 250.343
• InChiKey: TZLMQGIJGBCJHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (9ci)-1,5,6-三甲基-1H-苯并咪唑 、 对氯甲苯 在 NHC-Pd(II)-Im 、 potassium tert-butylate 作用下， 以 水 、 甲苯 为溶剂， 反应 6.0h， 以84%的产率得到1,5,6-Trimethyl-2-(4-methylphenyl)benzimidazole
  参考文献：
  名称：

  N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex-Catalyzed Direct C–H Bond Arylation of (Benz)imidazoles with Aryl Chlorides

  摘要：

  (Benz)imidazoles can be efficiently functionalized by (hetero)aryl chlorides via direct C-H bond arylation in the presence of a well-defined NHC-Pd(II)-Im complex. Under the optimal conditions, various activated, unactivated, and deactivated (hetero)aryl chlorides were successfully applied as the arylating reagents to achieve the 2-(hetero)aryl (benz)imidazoles in acceptable to high yields, giving a facile and alternative methodology for the direct C-H bond arylation of (benz)imidazoles.

  DOI：

  10.1021/jo5010058

文献信息

• Photoinduced C–H arylation of 1,3-azoles <i>via</i> copper/photoredox dual catalysis
  作者：Sven Trienes、Jiawei Xu、Lutz Ackermann

  DOI：10.1039/d4sc00393d

  日期：——

  The visible light-induced C–H arylation of azoles has been accomplished by dual-catalytic system with the aid of an inexpensive ligand-free copper(I)-catalyst in combination with a suitable photoredox catalyst. An organic photoredox catalyst, 10-phenylphenothiazine (PTH), was identified as effective, cost-efficient and environmentally-benign alternative to commonly-used, expensive Ir(III)-based complexes

  可见光诱导的唑类 C-H 芳基化反应是通过双催化系统借助廉价的无配体铜 ( I ) 催化剂与合适的光氧化还原催化剂的结合来完成的。有机光氧化还原催化剂 10-苯基吩噻嗪 (PTH) 被认为是常用、昂贵的 Ir( III ) 基络合物的有效、经济且环保的替代品。该方法被证明适用于各种唑衍生物的C-H芳基化，包括恶唑、苯并恶唑、噻唑、苯并噻唑以及更具挑战性的咪唑和苯并咪唑。此外，复杂分子的衍生化和天然产物Balsoxin的克级合成反映了所开发策略的合成效用。机理研究表明以芳基自由基为关键中间体的单电子转移（SET）机制。
• <i>N</i>-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex-Catalyzed Direct C–H Bond Arylation of (Benz)imidazoles with Aryl Chlorides
  作者：Zheng-Song Gu、Wen-Xin Chen、Li-Xiong Shao

  DOI：10.1021/jo5010058

  日期：2014.6.20

  (Benz)imidazoles can be efficiently functionalized by (hetero)aryl chlorides via direct C-H bond arylation in the presence of a well-defined NHC-Pd(II)-Im complex. Under the optimal conditions, various activated, unactivated, and deactivated (hetero)aryl chlorides were successfully applied as the arylating reagents to achieve the 2-(hetero)aryl (benz)imidazoles in acceptable to high yields, giving a facile and alternative methodology for the direct C-H bond arylation of (benz)imidazoles.