Nguyen Thi Ngoc Tran * , Lieu Ngoc Thien , Phan Thanh Son Nam , Dang Thi Hang and Dang Huynh Giao

* Correspondence: Nguyen Thi Ngoc Tran

Main Article Content

Abstract

Iron-organic framework MOF-235 was synthesized from 1,4-benzenedicarboxylic acid and iron(III) chloride by a solvothermal method. Physical characterizations of the solid catalyst were achieved by using a variety of different techniques. The  Fe-MOF was used as an productive heterogeneous catalyst for the synthesis of benzimidazoles via oxidative condensation of primary amines with 1,2-diaminoarenes.  The MOF-235 was found to be more catalytically active for the oxidative condensation of primary amines with 1,2-diaminoarenes than other MOFs. Leaching tests verified that the cyclization of 1,2-phenylenediamine with benzylamine to generate 2-phenyl-1H-benzo[d]imidazole was only possible in the presence of the iron-based framework catalyst, thus indicating that the transformation progressed via truly heterogeneous catalysis.
Keywords: 1, 2-diaminoarenes, benzimidazoles, condensation, cyclization, MOF-235

Article Details

References

Anbia, M., Hoseini, V., and Sheykhi, S., 2012. Sorption of methane, hydrogen and carbon dioxide on metal-organic framework, iron terephthalate (MOF-235). Journal of Industrial and Engineering Chemistry, 18(3): 1149-1152.

Cele, M.N., Friedrich, H.B, and Bala, M.D., 2014. Liquid phase oxidation of n-octane to C8 oxygenates over modified Fe-MOF-5 catalysts. Catalysis Communications, 57: 99-102.

Chae, H.K., Siberio-Perez, D.Y., Kim, J., et al., 2004. A route to high surface area, porosity and inclusion of large molecules in crystals. Nature, 427(6974): 523-527.

Chen, Y.-X., Qian, L.-F., Zhang, W. and Han, B., 2008. Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO. Angewandte Chemie International Edition, 47(48): 9330-9333.

Dhakshinamoorthy, A., and Garcia, H., 2012. Catalysis by metal nanoparticles embedded on metal–organic frameworks. Chemical Society Reviews, 41(15): 5262-5284.

Diao, X., Wang, Y., Jiang, Y., and Ma, D., 2009. Assembly of Substituted 1H-Benzimidazoles and 1,3-Dihydrobenzimidazol-2-ones via CuI/l-Proline Catalyzed Coupling of Aqueous Ammonia with 2-Iodoacetanilides and 2-Iodophenylcarbamates. Journal of Organic Chemistry, 74(20): 7974-7977.

Gopalaiah, K., and Chandrudu, S. N., 2015. Iron(II) bromide-catalyzed oxidative coupling of benzylamines with ortho-substituted anilines: synthesis of 1,3-benzazoles. RSC Advances, 5(7): 5015-5023.

Haque, E., Jun, J.W., and Jhung, S.H., 2011. Adsorptive removal of methyl orange and methylene blue from aqueous solution with a metal-organic framework material, iron terephthalate (MOF-235). Journal of Hazardous Materials, 185(1): 507-511.

Jusoh, N.W.C., Jalil, A.A., Triwahyono, S., and Mamat, C.R., 2015. Tailoring the metal introduction sequence onto mesostructured silica nanoparticles framework: Effect on physicochemical properties and photoactivity. Applied Catalysis A: General, 492: 169-176.

Kuppler, R.J., Timmons, D.J., Fang, Q.-R., Li, J.-R., Makal, T.A., Young, M.D., Yuan, D., Zhao, D. Zhuang, W., and Zhou, H.-C., 2009. Potential applications of metal-organic frameworks. Coordination Chemistry Reviews, 253(23-24): 3042-3066.

Leadbeater, N.E., and Marco, M., 2002. Preparation of Polymer-Supported Ligands and Metal Complexes for Use in Catalysis. Chemical Reviews, 102(10): 3217-3274.

Leus, K., Liu, Y.-Y., Meledina, M., Turner, S., Tendeloo, G.V., and Voort, P.V.D., 2014. A MoVI grafted Metal Organic Framework: Synthesis, characterization and catalytic investigations. Journal of Catalysis, 316: 201-209.

Liu, J., Chen, L., Cui, H., Zhang, J., Zhang, L., and Su, C.-Y., 2014. Applications of metal–organic frameworks in heterogeneous supramolecular catalysis. Chemical Society Reviews, 43(16): 6011-6061.

Lv, X., and Bao, W., 2009. Copper-Catalyzed Cascade Addition/Cyclization: An Efficient and Versatile Synthesis of N-Substituted 2-Heterobenzimidazoles. Journal of Organic Chemistry, 74(15): 5618-5621.

Mahesh, D., Sadhu, P., and Punniyamurthy, T., 2015. Copper(I)-Catalyzed Regioselective Amination of N-Aryl Imines Using TMSN3 and TBHP: A Route to Substituted Benzimidazoles. Journal of Organic Chemistry, 80(3): 1644-1650.

Mason, J.A., Veenstra, M., and Long, J.R., 2014. Evaluating metal–organic frameworks for natural gas storage. Chemical Science, 5(1): 32-51.

Noël, S., Cadet, S., Gras, E., and Hureau, C., 2013. The benzazole scaffold: a SWAT to combat Alzheimer's disease. Chemical Society Reviews, 42(19): 7747-7762.

Pizzetti, M., Luca, E.D., Petricci, E., Porcheddu, A., and Taddei, M. 2012. A General Approach to Substituted Benzimidazoles and Benzoxazoles via Heterogeneous Palladium-Catalyzed Hydrogen-Transfer with Primary Amines. Advanced Synthesis & Catalysis, 354(13): 2453-2464.

Singh, S., Bharti, N., and Mohapatra, P., 2009. Chemistry and natuarally occurring antiamoebic agents. Chemical Reviews, 109(5): 1900-1947.

Tranchemontagne, D.J., Ni, M.O.k. Z., and Yaghi, O.M., 2008. Reticular Chemistry of Metal–Organic Polyhedra. Angewandte Chemie International Edition, 47(28): 5136-5147.

Wang, K., Feng, D., Liu, T.-F., Su, J., Yuan, S., Chen, Y.-P., Bosch, M., Zou, X., and Zhou, H.-C., 2014. A Series of Highly Stable Mesoporous Metalloporphyrin Fe-MOFs. Journal of the American Chemical Society, 136(40): 13983-13986.

Xiao, T., Xiong, S., Xie, Y., Dong, X., and Zhou, L., 2013. Copper-catalyzed synthesis of benzazoles via aerobic oxidative condensation of o-amino/mercaptan/hydroxyanilines with benzylamines. RSC Advances, 3(36): 15592-15595.

Most read articles by the same author(s)