N,N-Dimethylbiguanide immobilized on mesoporous and magnetically separable silica: Highly selective and feasible organocatalyst for synthesis of β-nitroalcohols

Subject Areas : Iranian Journal of Catalysis

Gisya Abdi ¹ , Abdolhamid Alizadeh ² , Mohammad Khodaei ³ , Mustaffa Shamsuddin ⁴ , Sohrab Ghouzivand ⁵ , Mitra Fakhari ⁶ , Mojtaba Beygzadeh ⁷ , Amirhossein Fallah ⁸

1 - Department of Organic Chemistry, Faculty of Chemistry and Nanoscience& Nanotechnology Research Center (NNRC), Razi University, Kermanshah, 67149 Iran.
2 - Department of Organic Chemistry, Faculty of Chemistry and Nanoscience& Nanotechnology Research Center (NNRC), Razi University, Kermanshah, 67149 Iran. IbnuSina Institute for Fundamental Science Studies, Universiti Teknologi Malaysia, 81310 UTM, Johor Baharu, Johor, Malaysia.
3 - Department of Organic Chemistry, Faculty of Chemistry and Nanoscience& Nanotechnology Research Center (NNRC), Razi University, Kermanshah, 67149 Iran.
4 - IbnuSina Institute for Fundamental Science Studies, Universiti Teknologi Malaysia, 81310 UTM, Johor Baharu, Johor, Malaysia.
5 - Department of Organic Chemistry, Faculty of Chemistry and Nanoscience& Nanotechnology Research Center (NNRC), Razi University, Kermanshah, 67149 Iran.
6 - Department of Organic Chemistry, Faculty of Chemistry and Nanoscience& Nanotechnology Research Center (NNRC), Razi University, Kermanshah, 67149 Iran.
7 - Department of Organic Chemistry, Faculty of Chemistry and Nanoscience& Nanotechnology Research Center (NNRC), Razi University, Kermanshah, 67149 Iran.
8 - IbnuSina Institute for Fundamental Science Studies, Universiti Teknologi Malaysia, 81310 UTM, Johor Baharu, Johor, Malaysia.

Received: 2014-12-24 Accepted : 2015-02-25 Published : 2015-09-01

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References:

[1]     F. Hoffmann, M. Cornelius, J. Morell, M. Fröba, Angew. Chem. Int. Ed. 45 (2006) 3216-3251.
[2] X. Dong, Y. Hui, S. Xie, P. Zhang, G. Zhou, Z. Xie, RSC Adv. 3 (2013) 3222-3226.
[3] Z. Tao, RSC Adv. 4 (2014) 18961-18980.
[4] N. Gao, Y.-L. Chen, Y.-H. He, Z. Guan, RSC Adv. 3 (2013) 16850-16856.
[5] L. Henry and C. R. Seances, Acad. Sci. 120(1895)1265-1268.
[6] A.P. Piccionello, P. Pierro, A. Accardo, S. Buscemi, A. Pace, RSC Adv. 3 (2013)24946-24951.
[7] Y. Zhang, Z.J. Li, H.S. Xu, Y. Zhang, W. Wang, RSC Adv. 1 (2011) 389-392.
[8] R. Ballini, G. Bosica, J. Org. Chem. 62 (1997) 425-427.
[9] Y. Wei, L. Yao, B. Zhang, W. He, S. Zhang, Tetrahedron 67 (2011) 8552-8558.
[10] L. Yao, Y. Wei, P. Wang, W. He, S. Zhang, Tetrahedron 68 (2012) 9119-9124.
[11] R. Ballini, D. Fiorini, M.V. Gil, A. Palmieri, Tetrahedron 60 (2004) 2799-2804.
[12] M.N. Elinson, A.I. Ilovaisky, V.M. Merkulova, F. Barba, B. Batanero, Tetrahedron 64 (2008) 5915-
5919.
[13] R. Ballini, A. Palmieri, P. Righi, Tetrahedron 63 (2007) 12099-12121.
[14] J. Han, Y. Xu, Y. Su, X. She, X. Pan, Catal. Commun. 9 (2008) 2077-2079.
[15] T. Ishikawa, Superbases for organic synthesis: guanidines, amidines and phosphazenes and related organocatalysts, John Wiley & Sons, 2009.
[16] I. Kudyba, J. Raczko, Z. Urbańczyk-Lipkowska, J. Jurczak, Tetrahedron 60 (2004) 4807-4820.
[17] D. Simoni, R. Rondanin, M. Morini, R. Baruchello, F.P. Invidiata, Tetrahedron Lett. 41 (2000) 1607-1610.
[18] R. Mrówczyński, A. Nan, J. Liebscher, RSC Adv. 4 (2014) 5927-5952.
[19] Z. Zarnegar, J. Safari, RSC Adv. 4 (2014) 20932-20939.
[20] S. Shylesh, V. Schünemann, W.R. Thiel, Angew. Chem. Int. Ed. 49 (2010) 3428-3459.
[21] A. Hu, G.T. Yee, W. Lin, J. Am. Chem. Soc. 127 (2005) 12486-12487.
[22] V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.-M. Basset, Chem. Rev. 111 (2011) 3036-3075.
[23] A. Alizadeh, M. Khodaei, D. Kordestani, A. Fallah, M. Beygzadeh, Microporous Mesoporous Mater. 159 (2012) 9-16.
[24] A. Alizadeh, M. Khodaei, D. Kordestania, M. Beygzadeh, J. Mol. Catal. A: Chem. 372 (2013) 167-174.
[25] A. Alizadeh, M.M. Khodaei, M. Beygzadeh, D. Kordestani, M. Feyzi, Bull. Korean Chem. Soc. 33 (2012) 2547-2552.
[26] M. Beygzadeh, A. Alizadeh, M. Khodaei, D. Kordestani, Catal. Commun. 32 (2013) 86-91.
[27] N. Ono, The nitro group in organic synthesis, John Wiley & Sons, 2003.
[28] K. Dhahagani, J. Rajesh, R. Kannan, G. Rajagopal, Tetrahedron: Asymmetry 22 (2011) 857-865.
[29] Z.-L. Guo, S. Zhong, Y.-B. Li, G. Lu, Tetrahedron: Asymmetry 22 (2011) 238-245.
[30] X.-G. Liu, J.-J. Jiang, M. Shi, Tetrahedron: Asymmetry 18 (2007) 2773-2781.
[31] B. Subba Reddy, J. George, Tetrahedron: Asymmetry 22 (2011) 1169-1175.
[32] A. Cwik, A. Fuchs, Z. Hell, J.-M. Clacens, Tetrahedron 61 (2005) 4015-4021.
[33] V.J. Bulbule, V.H. Deshpande, S. Velu, A. Sudalai, S. Sivasankar, V. Sathe, Tetrahedron 55 (1999) 9325-9332.
[34] A. Noole, K. Lippur, A. Metsala, M. Lopp, T. Kanger, J. Org. Chem. 75 (2010) 1313-1316.
[35] L. Cheng, J. Dong, J. You, G. Gao, J. Lan, Chem. Eur. J. 16 (2010) 6761-6765.
[36] S. Selvakumar, D. Sivasankaran, V.K. Singh, Org. Biomol. Chem. 7 (2009) 3156-3162.