Nguyen Kim Chung * , Le Thanh Dung , Phan Thanh Son Nam , Tran Nhut Kien and Dang Huynh Giao

* Corresponding authorNguyen Kim Chung

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Abstract

Superparamagnetic copper ferrite nanoparticles were utilized as a recyclable heterogeneous catalyst for the cross-dehydrogenative coupling of N,N-disubstituted formamides with phenols. This routine allowed the creation of a hybrid benzothiazole-carbamate moiety under heterogeneous catalysis. These products possess both carbamate and benzothiazole moieties, thus taking profits from both structures with regard to pharmaceutical  and biological and activities.  Employing a catalytic portion of thesuperparamagneticnanoparticles, hybrid benzothiazole-carbamate structures could be produced with reasonable yields within 2 h. It was  possible to recover the nanoparticles by simple magnetic separation, and reutilize them for the reaction without a significant decline in catalytic efficiency. 
Keywords: Carbamates, formamides, nanocatalysis, nanoparticles, phenols

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References

Ali, W., Rout, S.K., Guin, S., Modi, A., Banerjee, A., and Patel, B.K., 2015. Copper-Catalyzed Dehydrogenative Coupling of N,N-Disubstituted Formamides and Phenols: A Direct Access to Carbamates. Advanced Synthesis & Catalysis. 357(2-3): 515-522.

Cano, R., Schmidt, A.F., and McGlacken, G.P., 2015. Direct arylation and heterogeneous catalysis; ever the twain shall meet. Chemical Science. 6(10): 5338-5346.

Dey, S., Gomes, R., Mondal, R. et al., 2015. Stable room temperature magnetic ordering and excellent catalytic activity of mechanically activated high surface area nanosized Ni0.45Zn0.55Fe2O4. RSC Advances. 5(96): 78508-78518.

Duan, H., Wang, D., and Li, Y., 2015. Green Chemistry for nanoparticle synthesis. Chemical Society Reviews. 44(16): 5778-5792.

Gawande, M.B., Goswami, A., Asefa, T. et al., 2015. Core-shell nanoparticles: synthesis and applications in catalysis and electrocatalysis. Chemical Society Reviews. 44(21): 7540-7590.

Hu, L., Zhang, R., and Chen, Q., 2014. Synthesis and assembly of nanomaterials under magnetic fields. Nanoscale. 6(23): 14064-14105.

Kathiresan, M., and Velayutham, D., 2015. Ionic liquids as an electrolyte for the electro synthesis of organic compounds. Chemical Communications. 51(99): 17499-17516.

Krogul, A., and Litwinienko, G., 2015. One pot synthesis of ureas and carbamates via oxidative carbonylation of aniline-type substrates by CO/O2 mixture catalyzed by Pd-complexes. Journal of Molecular Catalysis A: Chemistry. 407: 204-211.

Moghaddam, F.M., Tavakoli, G., Latifi, F. , and Saeednia, B., 2016. Nano cobalt ferrite cayalyzed coupling reaction of nitroarene and alkyl halide: An odorless and ligand-free rout to unsymmetrical thioether synthesis. Catalysis Communication. 94: 37-41.

Mohan, B., and Park, K.H., 2016. Supermagnetic copper ferrite nanoparticles catalyzed aerobic ligand-free, regioselective hydroborationof alkynes: influence of synergistic effect. Applied Catalysis A: General. 519: 78-84.

Nguyen, A.T., Pham, L.T., Phan, N.T.S., and Truong, T., 2014. Efficient and robust supermagnetic copper ferrite nanoparticle-catalyzed sequential methylation and C-H activation: aldehyde-free propargylamine synthesis. Catalysis Science & Technology. 4(12): 4281-4288.

Peiris, S., McMurtrie, J., and Zhu, H.-Y., 2016. Metal nanoparticle photocatalysts: emerging processes for green organic synthesis. Catalysis Science & Technology. 6(2): 320-338.

Purbia, R., and Paria, S., 2015. Yolk/shell nanoparticles: classifications, synthesis, properties, and applications. Nanoscale. 7(47): 19789-19873.

Rajesh, U.C., Divya, and Rawat, D.S., 2014. Functionalized supermagnetic Fe3O4 as an efficient quasi-homogeneous catalyst for multicomponent reactions. RSC Advances. 4(78): 41323-41330.

Ranganath, K.V.S., and Glorius, F., 2011. Superparamagnetic nanoparticles for asymmetric catalysis-a perfect match. Catalysis Science & Technology. 1(1): 13-22.

Reddy, N.V., Prasad, K.R., Reddy, P.S., Kantam, M.L., and Reddy, K.R., 2014. Metal free oxidative coupling of aryl formamides with alcohols for the synthesis of carbamates. Organic Biomolecular Chemistry. 12(14): 2172-2175

Saberi, D., Mansoori, S., Ghaderi, E., and Niknam, K., 2016. Copper nanoparticles on charcoal: an effective nanocatalyst for the synthesis of enol carbamates and amides via an oxidative coupling route. Tetrahedron Letter. 57(1): 95-99.

Sharma,N., Ojha, H., Bharadwaj, A., Pathak, D.P., and Sharma, R.K., 2015. Preparation and catalytic applications of nanoparticles: a review. RSC Advances. 5(66): 53381-53403.

Stark, W.J., Stoessel, P.R., Wohlleben, W., and Hafner, A., 2015. Industrial application nanoparticles. Chemical Society Reviews. 44(16): 5793-5805.

Wang, X.-X., Luo, M.-J., and Lu, J.-M., 2015. N-Heterocyclic carbene-palladium (II) -1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids. Organic Biomolecular Chemistry. 13(47): 11438-11444.

Zhang, Z.-c., Xu, B., and Wang, X., 2014. Engineering nanointerfaces for nanocatalysis. Chemical Society Reviews. 43(22): 7870-7886.

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