Silylation of alcohols and phenols by HMDS in the presence of ionic liquid and silica-supported ionic liquids

Authors

1 Department of Chemistry, Persian Gulf University, 75169, Boushehr, Iran. Department of Chemistry, University of Guilan, 41335/1914, Rasht, Iran.

2 Department of Chemistry, Persian Gulf University, 75169, Boushehr, Iran.

Abstract

In this research, different alcohols and phenols are subjected to the reaction with HMDS in the presence of ionic liquid and silica-supported catalysts. Silylation was accomplished under mild reaction conditions at room temperature in short reaction times and good to excellent yields.

Keywords


[1] N. Azizi, R. Yousefi, M.R. Saidi, J. Org.Chem. 691 (2006) 817–820.
[2] (a) S.H. Langer, S. Connell, J. Wender, J. Org. Chem. 23 (1958) 50-58. (b) P. Gauuret, S. El-Ghamarli, A. Legrand, D. Couirier, B. Rigo, Synth. Commun. 26 (1996) 707-713.
[3] F. Shirini, M.A. Zolfigol, K. Mohammadi, Phosphorus, Sulfur Silicon 178 (2003) 1567-1570.
[4] P. Kumar, V.R. Hedge, T.P. Kumar, Tetrahedron Lett. 36 (1995) 601-602.
[5] M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, Synth. Commun. 29 (1999) 541-546.
[6] N. Azizi, M.R. Saidi, Organometallics 23 (2004) 1457-1458.
[7] H. Firouzabadi, N. Iranpoor, A.A. Jafari, M.A. Jafari, J. Organomet. Chem. 693 (2008) 2711-2714.
[8] M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, Sh. Chahardahcheric, z. Tavakoli, J. Organomet. Chem. 693 (2008) 2041-2046.
[9] V.H. Tillu, V.H. Jadhav, H.B. Borate, R.D. Wakharkar, Arkivoc (2004) 83-88.
[10] F. Shirini, E. Mollarazi, Synth. Commun. 36 (2006) 1109-1115.
[11] H. Firouzabadi, N. Iranpoor, K. Amani, F. Nowrouzi, J. Chem. Soc. Perkin Trans. (2002) 2601-2604.
[12] R. Ghorbani-Vaghei, M.A. Zolfigol, M. Chegeny, H. Hojat, Tetrahedron Lett., 47 (2006) 4505–4508.
[13] H. Firouzabadi, B. Karimi, Synth. Commun. 23 (1993) 1633-1641.
[14] B. Akhlaghinia, S. Tavakoli, Synthesis (2005) 1775-1778.
[15] M.M. Mojtahedi, H. Abbasi, M.S. Abaee, J. Mol. Catal. A: Chem. 250 (2006) 6-8.
[16] H. Firouzabadi, N. Iranpoor, S. Sobhani, S. Ghassamipour, Synthesis (2005) 595–599.
[17] B. Karimi, B. Golshani, J. Org. Chem. 65 (2000) 7228-7230.
[18] A. Ghorbani-Choghamarani, M.A. Zolfigol, M. Hajjami, S. Jafari, J. Chin. Chem. Soc. 55 (2008) 1208-1213.
[19] H. Firouzabadi, N. Iranpoor, S. Sobhani, S. Ghassamipour, Z. Amoozgar, Tetrahedron Lett. 44 (2003) 891-893.
[20] H.R. Shaterian, F. Shahrekipoor, M. Ghashang, J. Mol. Catal. A: Chem. 272 (2007) 142-151.
[21] M.M. Mojtahedi, H. Abbasi, M.S. Abaee, Phosphorus, Sulfur Silicon 181 (2006) 1541-1544.
[22] D. Zareyee, B. Karimi, Tetrahedron Lett. 48 (2007) 1277–1280.
[23] A. Khazaei, M.A. Zolfigol, Z. Tanbakouchian, M. Shiri, K. Niknam, J. Saien, Catal. Commun. 8 (2007) 917-920.
[24] F. Shirini, K. Marjani, H.T. Nahzomi, M.A. Zolfigol, Phosphorus, Sulfur Silicon 182 (2007) 1245-1251.
[25] M.A. Zolfigol, G. Chehardoli, M. Dehghanian, K. Niknam, F. Shirini, J. Chin. Chem. Soc. 55 (2008) 885-889.
[26] K. Qiao, H. Hagiwara ,C.Yokoyama, J. Mol. Catal. A: Chem. 246 (2006) 65-69.
[27] R. Sugimura, K. Qiao, D. Tomida,C. Yokoyama, Catal. Commun. 8 (2007) 770-772.
[28] A. Chrobok, S. Baj, W. Pudlo, A. Jarzebski, Appl.Catal. A: Gen. 366 (2009) 22-28.
[29] M. NouriSefat, D. Saberi. K.Niknam, Catal.Lett. 141 (2011) 1713-1720.
[30] M. Baghernejad. K. Niknam, Int. J. Chem. 4 (2012) 52-60.
[31] (a) H.F. Lang, R.A. May, B.L. Iversenand, B.D. Chandler, J. Am. Chem. Soc. 125 (2003) 14832-14836. (b) H.F. Lang, S. Maldonado, K.J. Stevenson, B.D. Chandler, J. Am. Chem. Soc. 126 (2004) 12949-12956. (c) S.W. Kim, M. Kim, W.Y. Lee, T. Hyeon, J. Am. Chem. Soc. 124 (2002) 7642-7643. (d) K.H. Park, S.U. Son, Y.K. Chung, Org. Lett. 4 (2002) 4361-4363. (e) T.G. Galow, U. Dreshler, J.A. Hanson, V.M. Rotello, Chem. Commun. (2002) 1076-1077. (f) C.M. Crudden,M. Sateesh, R. Lewis, J. Am. Chem. Soc.127 (2005) 10045-10050.
[32] H. Tajik, Kh. Niknam, F. Parsa, J. Iran. Chem. Soc. 6 (2009) 159-164.
[33] (a) A. Khazaei, M.A. Zolfigol, Z. Tanbakouchian, M. Shiri, K. Niknam, J. Saien, Catal. Commun. 8 (2007) 917-920. (b) A. Khazaei, M.A. Zolfigol, A. Rostami, Catal. Commun. 8 (2007) 543-547.
[34] M.M. Mojtahedi, M. Abaee, V. Hamidi, A. Zolfaghari, Ultrason. Sonochem. 14 (2007) 596-598.
[35] J.L. Speier, J. Am. Chem. Soc., 74 (1952) 1003-1010.
[36] G.A. Oalh, T.D. Ernst, J. Org. Chem. 54 (1989) 1204-1206.
[37] S.T. Kadam, S.S. Kim, J. Organometal. Chem. 694 (2009) 2562-2566.
[38] C.B. Yue, T.F. Yi, C.B. Zhu, G. Liu, J. Indus. Engin. Chem. 15 (2009) 653-656.
[39] H. Qiu, Q. Jiang, Z. Wei, X. Wang, X. Liu, S. Jiang, J. Chrom. A. 1163 (2007) 63-69.
[40] A. Chrobok, S. Baj, W. Pudlo, A. Jarzebski, Appl. Catal. A: Gen. 366 (2009) 22-28.