Regioselective conversion of epoxides to vicinal nitrohydrins catalyzed by silica-bound 3-{2-[poly(ethylene glycol)]ethyl}-substituted 1-methyl-1H-imidazol-3-ium bromide as a green and reusable catalyst under aqueous thermal conditions

Iranian Journal of Catalysis

مقاله 5، دوره 8، شماره 3، آذر 2018، صفحه 195-202   

نوع مقاله: Articles

نویسندگان

Neda Ayashi¹؛ Mehdi Fallah-Mehrjardi^{2، 3}؛ Ali Reza Kiasat^{* 1}

¹Department of Chemistry, College of Science, Shahid Chamran University of Ahvaz, P.O. Box 61357-4-3169, Ahvaz, Iran.

²Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.

³Research Center of Environmental Chemistry, Payame Noor University, Ardakan, Yazd, Iran.

چکیده

An environmentally benign procedure for the synthesis of vicinal nitrohydrins via the regioselective ring opening reaction of epoxides with nitrite anion using silica-bound 3-{2-[poly(ethylene glycol)]ethyl}-substituted 1-methyl-1H-imidazol-3-ium bromide as an effective heterogeneous phase transfer catalyst was described. Short reaction time, high yield of products, simple work-up procedure, and recyclability of the catalyst were some of the striking features of the present protocol. The recovered catalyst could be reused five times without any loss in its catalytic activity and selectivity.

کلیدواژه‌ها

2-Nitroalcohols؛ Phase transfer catalyst؛ Ring opening of epoxides؛ Regioselective؛ green chemistry

مراجع

[1] N. Ono, The nitro group in organic synthesis, Wiley-VCH, New York, 2001.
[2] D.J. Ager, I. Prakash, D. Schaad, Chem. Rev. 96 (1996) 835–876.
[3] Y. Bleriot, N. Auberger, Y. Jagadeesh, C. Gauthier, G. Prencipe, A.T. Tran, J. Marrot, J. Desire, A. Yamamoto, A. Kato, M. Sollogoub, Org. Lett. 16 (2014) 5512-5515.
[4] D.M. Coe, P.L. Myers, D.M. Parry, S.M. Roberts, R. Storerb, J. Chem. Soc. Chem. Commun. (1990) 151–154.
[5] T. Suami, K.I. Tadano, A. Suga, Y. Ueno, J. Carbohyd. Chem. 3 (1984) 429–441.
[6] B. Kalita, N.C. Barua, M. Bezbarua, G. Bez, Synlett (2001) 1411-1414.
[7] B. Tamami, N. Iranpoor, R. Rezaie, Iran. Polym. J. 13 (2004) 495-501.
[8] N. Iranpoor, H. Firouzabadi, M. Shekarize, Org. Biomol. Chem. 1 (2003) 724-727.
[9] H. Mahdavi, B. Tamami, React. Funct. Polym. 64 (2005) 179–185.
[10] J.C. Borah, S. Gogoi, J. Boruwa, N.C. Barua, Synth. Commun. 35 (2005) 873-878.
[11] F. Ebrahimzadeh, R. Rooydell, Chem. Sin. 3 (2012) 1146-1152.
[12] M. Doble, A.K. Kruthiventi, Green chemistry and engineering, Academic Press, 2007.
[13] E. Murugan, G. Tamizharasu, P. Shanmugam, React. Kinet. Mech. Cat. 113 (2014) 39-59.
[14] D. Xin, J. Yuan, K.Y. Wong, K. Burgess, J. Org. Chem. 81 (2016) 8071-8081.
[15] S. Sayyahi, S. Heidari, Iran. J. Catal. 6 (2016) 167-172.
[16] A.R. Kiasat, N. Ayashi, M. Fallah-Mehrjardi, Helv. Chim. Acta 96 (2013) 275-279.
[17] A.R. Kiasat, N. Ayashi, M. Fallah-Mehrjardi, J. Iran. Chem. Soc. 10 (2013) 1175–1181.
[18] A.R. Kiasat, M. Fallah-Mehrjardi, Catal. Commun. 9 (2008) 1497–1500.
[19] A.R. Kiasat, R. Mirzajani, H. Shalbaf, T. Tabatabaei, M. Fallah-Mehrjardi, J. Chin. Chem. Soc. 56 (2009) 594-599.
[20] A.R. Kiasat, F. Ataeian, M. Fallah-Mehrjardi, Iran. J. Catal. 2 (2012) 1-5.
[21] A.R. Kiasat, F. Chadorian, S.J. Saghanezhad, C.R. Chim. 18 (2015) 1297-1306.
[22] F. Moheiseni, A.R. Kiasat, Iran. J. Catal. 7 (2017) 153-159.
[23] H. Firouzabadi, N. Iranpoor, B. Karimi, H. Hazarkhami, Synlett (2000) 263-265.
[24] S. Grinberg, E. Shaubi, Tetrahedron 47 (1991) 2895-2902.
[25] G. Hasnaoui, J.H.L. Spelberg, E. Vries, L. Tang, B. Hauer, D.B. Janssen, Tetrahedron: Asymmetry 16 (2005) 1685–1692.