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
相关论文
共 55 条
[1]   A review on conversion of biomass to biofuel by nanocatalysts [J].
Akia, Mandana ;
Yazdani, Farshad ;
Motaee, Elahe ;
Han, Dezhi ;
Arandiyan, Hamidreza .
BIOFUEL RESEARCH JOURNAL-BRJ, 2014, 1 (01) :16-25
[2]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[3]  
[Anonymous], 2011, J CHEM PHARM RES
[4]   Palladium catalyst supported on PEGylated imidazolium based phosphinite ionic liquid-modified magnetic silica core-shell nanoparticles: a worthy and highly water-dispersible catalyst for organic reactions in water [J].
Bahadorikhalili, Saeed ;
Ma'mani, Leila ;
Mahdavi, Hossein ;
Shafiee, Abbas .
RSC ADVANCES, 2015, 5 (87) :71297-71305
[5]   Electronic confinement and coherence in patterned epitaxial graphene [J].
Berger, Claire ;
Song, Zhimin ;
Li, Xuebin ;
Wu, Xiaosong ;
Brown, Nate ;
Naud, Cecile ;
Mayou, Didier ;
Li, Tianbo ;
Hass, Joanna ;
Marchenkov, Atexei N. ;
Conrad, Edward H. ;
First, Phillip N. ;
de Heer, Wait A. .
SCIENCE, 2006, 312 (5777) :1191-1196
[6]   Predesigned Metal-Anchored Building Block for In Situ Generation of Pd Nanoparticles in Porous Covalent Organic Framework: Application in Heterogeneous Tandem Catalysis [J].
Bhadra, Mohitosh ;
Sasmal, Himadri Sekhar ;
Basu, Arghya ;
Midya, Siba P. ;
Kandambeth, Sharath ;
Pachfule, Pradip ;
Balaraman, Ekambaram ;
Banerjee, Rahul .
ACS APPLIED MATERIALS & INTERFACES, 2017, 9 (15) :13785-13792
[7]   Human β3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides [J].
Brockunier, LL ;
Parmee, ER ;
Ok, HO ;
Candelore, MR ;
Cascieri, MA ;
Colwell, LF ;
Deng, LP ;
Feeney, WP ;
Forrest, MJ ;
Hom, GJ ;
MacIntyre, DE ;
Tota, L ;
Wyvratt, MJ ;
Fisher, MH ;
Weber, AE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (18) :2111-2114
[8]   Cyclodextrins in drug delivery: An updated review [J].
Challa, R ;
Ahuja, A ;
Ali, J ;
Khar, RK .
AAPS PHARMSCITECH, 2005, 6 (02)
[9]   n-Octyl alcohol dehydrogenation over copper catalysts [J].
Crivello, Monica E. ;
Perez, Celso F. ;
Mendieta, Silvia N. ;
Casuscelli, Sandra G. ;
Eimer, Griselda A. ;
Elias, Veronica R. ;
Herrero, Eduardo R. .
CATALYSIS TODAY, 2008, 133 :787-792
[10]   Coupling biocatalysis and click chemistry: one-pot two-step convergent synthesis of enantioenriched 1,2,3-triazole-derived diols [J].
Cuetos, Anibal ;
Bisogno, Fabricio R. ;
Lavandera, Ivan ;
Gotor, Vicente .
CHEMICAL COMMUNICATIONS, 2013, 49 (26) :2625-2627