Regioselective conversion of epoxides to β-acetoxy alcohols catalyzed by a novel green and recyclable phase transfer catalyst

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Abstract

A new mild and efficient procedure for the ring opening of epoxides by acetate anion in the presence of catalytic amounts of silica-bound polyethylene glycol substituted 1-methylimidazolium bromide, SiO2-PEG-ImBr, as an effective heterogeneous phase transfer catalyst in aqueous media is developed. A variety of β-acetoxy alcohols are obtained in high yields with excellent regioselectivity in short reaction times. The remarkable features of this procedure are improved yields, high regioselectivity, small quantity of catalyst, easy work-up, ease of recyclability of catalyst and environmentally friendliness. The recycled catalyst could be reused over four times with almost no loss of catalytic activity.
A new mild and efficient procedure for the ring opening of epoxides by acetate anion in the presence of catalytic amounts of silica-bound polyethylene glycol substituted 1-methylimidazolium bromide, SiO2-PEG-ImBr, as an effective heterogeneous phase transfer catalyst in aqueous media is developed. A variety of β-acetoxy alcohols are obtained in high yields with excellent regioselectivity in short reaction times. The remarkable features of this procedure are improved yields, high regioselectivity, small quantity of catalyst, easy work-up, ease of recyclability of catalyst and environmentally friendliness. The recycled catalyst could be reused over four times with almost no loss of catalytic activity.

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References

[1] C.J. Li, T.H. Chan “Comprehensive organic reactions in aqueous media”, John Wiley & Sons, Hoboken, 2nd Ed., (1997).
[2]  هنرمند، مونس; مجله شیمی کاربردی دانشگاه سمنان، ویژه نامه نخستین سمینار شیمی کاربردی ایران، (1395) ص 41.
[3]  ملکی، بهروز; طیبی، رضا; بقایری، مهدی; نصرآبادی، زهرا، مجله شیمی کاربردی دانشگاه سمنان، شماره 43 (1396) ص 81.
[4] C.M. Starks, C.L. Liotta, M. Halpern “Phase-transfer catalysis”, Chapman and Hall, New York, 1st Ed., (1994).
[5] N. Mizuno, M. Misono, Chem. Rev. 98 (1998) 199.
[6] E.J. Corey, S. Shibata, R.K. Bakshi, J. Org. Chem. 53 (1988) 2861.
[7] A.R. Kiasat, R. Mirzajani, H. Shalbaf, T. Tabatabaei, M. Fallah-Mehrjardi, J. Chin. Chem. Soc. 56 (2009) 594.
[8] A.R. Kiasat, M. Fallah-Mehrjardi, Catal. Commun. 9 (2008) 1497.
[9] A. Kamal, G.B.R. Khanna, R. Ramu, Tetrahedron: Asy. 13 (2002) 2039.
[10]  J.C. Borah, S. Gogoi, J. Boruwa, N.C. Barua, Synth. Commun., 35 (2005) 873.
[11]  B. Tamami, N. Iranpoor, R. Rezaie, Iran. Polym. J. 13 (2004) 495.
[12]  G.D. Yadav, S. Singh, Tetrahedron Lett. 55 (2014) 3979.
[13]  G. Xie, L. Xu, J. Hu, S. Ma, W. Hou, , F. Tao, Tetrahedron Lett. 29 (1988) 2967.
[14]  N. Iranpoor, I. Mohammadpour-Baltork, F. Shiriny Zardaloo, Tetrahedron, 47 (1991) 9861.
[15] A. Mohammadpoor-Baltork, S. Tangestaninejad, H. Aliyan, V. Mirkhani, Synth. Commun. 30 (2000) 2365.
[15]  R.-H. Fan, X.-L. Hou, Tetrahedron Lett. 44 (2003) 4411.
[16]  V. Mirkhani, S. Tangestaninejad, B. Yadollahi, L. Alipanah, Tetrahedron, 59 (2003) 8213.
[17]  H. Firouzabadi, N. Iranpoor, A.A. Jafari, S. Makarem, J. Mol. Catal. A: Chem. 250 (2006) 237.
[18] M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S.A. Taghavi, Catal. Commun. 8 (2007) 2087.
[19] E. Alvarez-Manzaneda, R. Chahboun, E. Alvarez, R. Alvarez-Manzaneda, P.E. Muñoz, F. Jiménez, H. Bouanou, Tetrahedron Lett. 52 (2011) 4017.
[20] A.R. Kiasat, M. Zayadi, Catal. Commun. 9 (2008) 2063.
[21] A.R. Kiasat, R. Badri, B. Zargar, S. Sayyahi, J. Org. Chem. 73 (2008) 8382.
[22] A.R. Kiasat, N. Ayashi, M. Fallah-Mehrjardi, Helv. Chim. Acta, 96 (2013) 275.
[23] A.R. Kiasat, N. Ayashi, M. Fallah-Mehrjardi, J. Iran. Chem. Soc. 10 (2013) 1175.
[24] S. Grinberg, E. Shaubi, Tetrahedron, 47 (1991) 2895.
Applied Chemistry Today
Volume 13, Issue 47
June 2018
Pages 59-68

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