Copper supported β-cyclodextrin functionalized PEGylated mesoporous silica nanoparticle-graphene oxide hybrid: An efficient and recyclable nano-catalyst for straightforward synthesis of 2-arylbenzimidazoles and 1,2,3-triazoles

被引:76
作者
Bahadorikhalili, Saeed [1 ]
Ma'mani, Leila [2 ]
Mahdavi, Hossein [1 ]
Shafiee, Abbas [3 ,4 ]
机构
[1] Univ Tehran, Coll Sci, Sch Chem, POB 14155-6455, Tehran, Iran
[2] AREEO, ABRII, Dept Nanotechnol, Karaj, Iran
[3] Univ Tehran Med Sci, Fac Pharm, Tehran, Iran
[4] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran, Iran
关键词
Air oxidation; Click reaction; Cu catalyst; Mesoporous silica nanoparticles-graphene oxide hybrid; ONE-POT SYNTHESIS; PHARMACEUTICAL APPLICATIONS; BIS-BENZIMIDAZOLES; ORGANIC-REACTIONS; TERMINAL ALKYNES; BORONIC ACIDS; SODIUM-AZIDE; WATER; NANOCATALYST; SOLVENT;
D O I
10.1016/j.micromeso.2017.11.046
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
beta-Cyclodextrin functionalized PEGylated mesoporous silica nanoparticles-graphene oxide hybrid has been introduced as a heterogeneous support for immobilization of copper catalyst (denoted as Cu@beta CD-PEG-mesoGO). Mesoporous silica nanoparticles-graphene oxide hybrid (mesoGO) was synthesized and functionalized by PEG(600) ended beta-cyclodextrin. Then, Cu was immobilized onto the later modified nanoparticles. Cu@beta CD-PEG-mesoGO was evaluated for the synthesis of benzimidazoles and 1,2,3-triazoles. The synthesis of 2-aryl benzimidazole derivatives from o-phenylenediamines and benzaldehydes via aerobic C-N bond oxidation reaction was successfully performed using Cu@beta CD-PEG-mesoGO as a green catalyst. The catalyst was also applied for the synthesis of 1,2,3-triazole derivatives via three component click reaction of alkynes, benzylbromides and sodium azide. The catalyst recovery test was performed, and showed that this catalyst is highly reusable without a significant decrease in its activity. This catalyst has outstanding properties such as high efficiency and turnover frequency (TOF), simple product work-up, utilization of H2O as a green solvent, mild reaction conditions, and easy catalyst recovery.
引用
收藏
页码:207 / 216
页数:10
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