Sulfuric acid ([3-(3-silicapropyl)-sulfanyl]propyl)ester as recyclable catalyst for the silylation of hydroxyl groups
الموضوعات : Iranian Journal of CatalysisFarid Rohandeh 1 , Dariush Saberi 2 , Khodabakhsh Niknam 3
1 - Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.
2 - Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169 Iran.
3 - Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.
Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169 Iran.
الکلمات المفتاحية: Catalyst, Silylation, Hydroxyl group, Sulfuric acid ([3-(3-silicapropyl)sulfanyl]propyl)ester, Heterogenous solid acid,
ملخص المقالة :
Sulfuric acid ([3-(3-silicapropyl)sulfanyl]propyl]ester (SASPSPE) is employed as a recyclable catalyst for the silylation of hydroxyl groups. A good range of primary, secondary alcohols and phenolic hydroxyl groups were effectively converted into their corresponding trimethylsilyl ethers with hexamethyldisilazane in the presence of catalytic amounts of SASPSPE at room temperature with short reaction times in good to excellent yields. This heterogeneous catalyst was recycled for nine runs without losing its catalytic activity.
[1] A. Corma, Adv. Mater. 7 (1995) 137-144.
[2] M. A. Harmer, Q. Sun, Appl. Catal. A: Gen. 221 (2001) 45-62.
[3] T. Okuhara, Chem. Rev. 102 (2002) 3641-3666.
[4] K. Arata, H. Matsuhashi, M. Hino, H. Nakamura, Catal. Today 81 (2003) 17-30.
[5] D. Zareyee, B. Karimi, Tetrahedron Lett. 48 (2007) 1277-1280.
[6] J. A. Melero, R. V. Grieken, G. Morales, Chem. Rev. 106 (2006) 3790-3812.
[7] (a) K. Niknam, D. Saberi, Appl. Catal. A: Gen. 366 (2009) 220-225. (b) K. Niknam, D. Saberi, M. Nouri Sefat, Tetrahedron Lett. 50 (2009) 4058-4062. (c) K. Niknam, D. Saberi, M. Mohagheghnejad, Molecules 14 (2009) 1915-1926. (d) K. Niknam, D. Saberi, M. Baghernrjad, Chin. Chem. Lett. 20 (2009) 1444-1448 (e) K. Niknam, D. Saberi, Tetrahedron Lett. 50 (2009) 5210-5214. (f) K. Niknam, D. Saberi, M. Sadegheyan, A. Deris, Tetrahedron Lett. 51 (2010) 692-694. (g) K. Niknam, D. Saberi, M. Nouri Sefat, Tetrahedron Lett. 51 (2010) 2959-2962.
[8] K. Niknam, M. A. Zolfigol, A. Khorramabadi-Zad, R. Zare, M. Shayegh, Catal. Commun. 7 (2006) 494-498. (b) K. Niknam, B. Karami, M. A. Zolfigol, Catal. Commun. 8 (2007) 1427-1430. (c) K. Niknam, M. A. Zolfigol, T. Sadabadi, J. Iran. Chem. Soc. 4 (2007) 199-204. (d) K. Niknam, M. A. Zolfigol, Z. Hossieninejad, N. Daneshvar, Chin. J. Catal. 28 (2007) 591-595. (e) K. Niknam, M. A. Zolfigol, T. Sadabadi, A. Nejati, J. Iran. Chem. Soc. 3 (2006) 318-322.
[9] (a) K. Niknam, D. Saberi, M. Baghernejad, Phosphorus, Sulfur and Silicon 185 (2010) 875-882. (b) K. Niknam, F. Panahi, D. Saberi, M. Mohagheghnejad, J. Heterocycl. Chem. 47 (2010) 292-300. (c) K. Niknam, M. R. Mohammadizadeh, S. Mirzaee, D. Saberi, Chin. J. Chem. 28 (2010) 663-669. (d) F. Rashedian, D. Saberi, K. Niknam, J. Chin. Chem. Soc. 57 (2010) 998-1006. (e) K. Niknam, N. Jafarpour, E. Niknam, Chin. Chem. Lett. 22 (2011) 69-72. (f) K. Niknam, M. R. Mohammadizadeh, S. Mirzaee, Chin. J. Chem. 29 (2011) 2421-2427. (g) K. Niknam, S. Mirzaee, Synth. Commun. 41 (2011) 2403-2413.
[10] T. W. Greene, P. G. M. Wutes, Greene’s Protective Groups in Organic Synthesis, fourth ed., Wiley, New York, 2007.
[11] S. H. Langer, S. Connell, J. Wender, J. Org. Chem. 23 (1958) 508-508.
[12] T. Morita, Y. Okamoto, H. Sakurai, Tetrahedron Lett. 21 (1980) 835-838.
[13] B. Hatano, S. Toyota, F. Toda, Green Chem. (2001) 140-142.
[14] T. Watahiki, M. Matsuzaki, T. Oriyama, Green Chem. (2003) 82-84.
[15] X. Huang, C. Craita, L. Awad, P. Vogel, Chem. Commun. (2005) 1297-1299.
[16] F. Shirini, M. A. Zolfigol, M. Paktinat, Synthesis (2006) 4252-4256.
[17] C. A. Bruynes, T. K. Jurriens, J. Org. Chem. 47 (1982) 3966-3969.
[18] A. Khazaei, M. A. Zolfigol, A. Rostami, A. Ghorbani Choghamarani, Catal. Commun. 8 (2007) 543-547.
[19] H. Firouzabadi, N. Iranpoor, K. Amani, F. Nowrouzi, J. Chem. Soc., Perkin Trans.1, (2002) 2601-2604.
[20] Z. H. Zhang, T. S. Li, F. Yang, C. G. Fu, Synth. Commun. 28 (1998) 3105-3114.
[21] N. Azizi, M. R. Saidi, Organometallics 23 (2004) 1457-1458.
[22] B. Akhlaghinia, S. Tavakoli, Synthesis (2005) 1775-1778.
[23] V. H. Tillu, V. H. Jadhav, H. B. Borate, R. D. Wakharkar, Arkivoc 14 (2004) 83-88.
[24] M. M. Mojtahedi, H. Abbasi, M. S. Abaee, J. Mol. Catal. A: Chem. 250 (2006) 6-8.
[25] H. R. Shaterian, F. Shahrekipoor, M. Ghashang, J. Mol. Catal. A: Chem. 272 (2007) 142-151.
[26] H. R. Shaterian, F. Khorami, A. Amirizadeh, M. Ghashang, A. Hosseinian, Phosphorus Sulfur Silicon 183 (2008) 2584-2595.
[27] D. Zareyee, B. Karimi, Tetrahedron Lett. 48 (2007) 1277-1280.
[28] H. Ghafuri, B. Eftekhari-Sis, M. M. Hashemi, Phosphorus Sulfur Silicon 182 (2007) 1645-1651.
[29] A. Ghorbani-Choghamarani, M. A. Zolfigol, M. Hajjami, S. Jafari, J. Chin. Chem. Soc. 55 (2008) 1208-1213.
[30] A. Khazaei, M. A. Zolfigol, Z. Tanbakouchian, M. Shiri, K. Niknam, J. Saien, Catal. Commun. 8 (2007) 917-920.
[31] K. Niknam, M. A. Zolfigol, G. Chehardoli, M. Dehghanian, Chin. J. Catal. 29 (2008) 901-906.
[32] M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S. Chahardahcheric, Z. Tavakoli, J. Organometal. Chem. 693 (2008) 2041-2046.
[33] F. Shirini, M. Abedini, J. Iran. Chem. Soc. 5 (2008) S87-S90.
[34] K. Niknam, M. A. Zolfigol, D. Saberi, H. Molaee, J. Chin. Chem. Soc. 56 (2009) 1257-1264.
[35] K. Niknam, D. Saberi, H. Molaee, M. A. Zolfigol, Can. J. Chem. 88 (2010) 164-171.
[36] M. A. Zolfigol, E. Kolvari, N. Koukabi, S. Salehzadeh, G. Chehardoli, I. S. Tidmarsh, K. Niknam, J. Iran. Chem. Soc. 8 (2011) 484-494.
[37] M. G. Dekamin, N. Yazdaninia, J. Mokhtari, M. R. Naimi-Jamal, J. Iran. Chem. Soc. 8 (2011) 537-544.
[38] S. H. Lee, S. T. Kadam, Appl. Organometal. Chem. 25 (2011) 608-615.
