Brönsted acidic ionic liquid ([Hmim][HSO4]) as a green, efficient and reusable catalyst for the tetrahydropyranylation of alcohols

Iranian Journal of Catalysis

مقاله 4، دوره 2، شماره 1، فروردین 2012، صفحه 23-26   

نویسندگان

Abdol R. Hajipour^{* 1}؛ Fatemeh Rafiee²

¹Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, IRAN Department of Pharmacology, University of Wisconsin Medical School, 1300 University Avenue, Madison, WI, USA 53706-1532

²Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, IRAN

چکیده

A simple and mild method for tetrahydropyranylation of alcohols is reported at room temperature using a catalytic amount of 3-methylimidazolinium hydrogensulfate([Hmim]HSO₄) as a green, efficient and reusable catalyst. Using solvent-free conditions, non-toxic and inexpensive materials, modest and clean work-up, short reaction times and high yields of the products are the advantages of this method.

کلیدواژه‌ها

Brönsted acidic ionic liquids؛ Catalyst؛ Tetrahydropyranylation؛ Alcohols

مراجع

[1] Z. Du, Z. Li, Y. Gu, J. Zhang, Y. Deng, J. Mol. Catal. A: Chem. 237 (2005) 80-85.

[2] A. R. Hajipour, F. Rafiee, A. E. Ruoho, J. Iran. Chem. Soc. 7 (2010) 114-118.

[3] A. R. Hajipour, F. Rafiee, A. E. Ruoho, Synth. Commun. 17 (2006) 2563-2568.

[4] A. R. Hajipour, F. Rafiee, J. Iran. Chem. Soc. 6 (2009) 647-678.

[5] A. R. Hajipour, F. Rafiee, A. Ruoho, Synth. Commun. (2011) 603-611.

[6] L. Khazdooz, A. Zarei, A. R. Hajipour, N. Sheikhan, Iran. J. Catal. 1 (2011) 1-9.

[7] A. R. Hajipour, F. Rafiee, Appl. Organomet. Chem. 25 (2011) 542-551.

[8] A. R. Hajipour, F. Rafiee, Org. Prep. Proced. Int. 42 (2010) 285-362.

[9] S. Sahoo, T. Joseph, S. B. Halligudi, J. Mol. Catal. A: Chem. 244 (2006) 179-182.

[10] J. Z. Gui, X. H. Cong, D. Liu, X. T. Zhang, Z. T. Hu, Z. L. Sun, Catal. Commun. 5 (2004) 473-477.

[11] A. R. Hajipour, G. Azizi, A. E. Ruoho, Synlett, 12 (2009) 1974-1978.

[12] A. R. Hajipour, Z. Nasreesfahani, A. E. Ruoho, Org. Prep. Proced. Int. 40 (2008) 385-391.

[13] G. Driver, K. E. Johnson, Green Chem., 5 (2003) 163-169.

[14] A. R. Hajipour, F. Rafiee, A. E. Ruoho, Synlett 7 (2007) 1118-1120.

[15] A. R. Hajipour, G. Azizi, A. E. Ruoho, Synth. Commun. 39 (2009) 242-250.

[16] A. R. Hajipour, L. Khazdooz, A. E. Ruoho, J. Chin. Chem. Soc. 56 (2009) 398-403.

[17] A. R. Hajipour, A. Rajaei, A. E. Ruoho, Tetrahedron Lett. 50 (2009) 708-711.

[18] A. R. Hajipour, Y. Ghayeb, N. Sheikhan, A. E. Ruoho, Synlett 5 (2010) 741-744.

[19] T. W. Greene, P. G. M. Wuts, Protective groups in organic synthesis, third ed., John Wiley & Sons, New York, 1999.

[20] P. J. Kocienski, Protecting groups, Georg Thieme Verlag, New York, 2000.

[21] M. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chem. 42 (1977) 3772-3774.

[22] A. R. Hajipour, M. Kargosha, A. E. Ruoho, Synth. Commun. 39 (2009) 1084-1091.

[23] Y. S. Hon, C. F. Lee, Tetrahedron Lett. 40 (1999) 2389-2392.

[24] H. M. Kumar, B. V. Reddy, E. J. Reddy, J. S. Yadav, Chem. Lett. (1999) 857-858.

[25] N. Rezai, F. A. Meybodi, P. Salehi, Synth. Commun. 30 (2000) 1799-1805.

[26] S. Naik, R. Gopinath, B. K. Patel, Tetrahedron Lett. 42 (2001) 7679-7681.

[27] M. M. Heravi, F. K. Behbahani, A. H. Oskooie, R. H. Shoar, Tetrahedron Lett. 46 (2005) 2543-2545.

[28] M. H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork, V. Mirkhani, B. Yadollahi, Tetrahedron Lett. 42 (2001) 2851-2853.

[29] A. R. Hajipour, S. A. Pourmousavi, A. E. Ruoho, Synth. Commun. 35 (2005) 2889-2894.

[30] Y. G. Wang, X. X. Wu, Z. Y. Jiang, Tetrahedron Lett. 45 (2004) 2973-2976.

[31] H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Synth. Commun. 34 (2004) 3623-3630.

[32] D. M. Pore, U. V. Desai, R. B. Mane, P. P. Wadgaonkar, Synth. Commun. 34 (2004) 2135-2142.

[33] A. T. Khan, S. Ghosh, L. H. Choudhury, Eur. J. Org. Chem. (2005) 4891-4896.

[34] S. Islam, A. Majee, A. T. Khan, Synth. Commun. 35 (2005) 1789-1793.

[35] V. V. Namboodiri, R. S. Varma, Tetrahedron Lett. 43 (2002) 1143-1146.

[36] A. Khazaei, A. Rostami, M. Mahboubifar, Catal. Commun. 8 (2007) 383-388.

[37] P. S. Poon, A. K. Banerjee, L. Bedoya, M. S. Laya, E. V. Cabrera, K. M. Albornoz, Synth. Commun. 39 (2009) 3369-3377.

[38] V. Kavala, A. K. Samal, B. K. Patel, Arkivoc (2005) 20-29.

[39] P. P. Sun, Z. X. Hu, Chin. J. Chem. 22 (2004) 1341-1343.

[40] a) S. G. Pyne, A. R. Hajipour, Tetrahedron 48 (1992) 9385-9390; b) A.R. Hajipour, G. Mazloumi, Synth. Commun. 32 (2002) 23-30; c) A. R. Hajipour, S. E. Mallakpour, I. M. Baltork, H. Adibi, Synth. Commun. 31 (2001) 1625-1631; d) A. R. Hajipour, S. E. Mallakpour, I. M. Baltork, K. Niknam, Org. Prep. Proced. Int. 31 (1999) 335-341.