1,1’-(Ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) as an organocatalyst for the silylation/desilylation reaction
الموضوعات : Iranian Journal of CatalysisGholamabbas Chehardoli 1 , Mohammad Zolfigol 2 , Tahereh Azadbakht 3
1 - School of Pharmacy, Hamedan University of Medical Sciences, Zip Code 65178 Hamedan, Iran
2 - Faculty of Chemistry, Bu-Ali Sina University, P. O. Box 6517838683
3 - Faculty of Chemistry, Bu-Ali Sina University, P. O. Box 6517838683.
الکلمات المفتاحية: 1, Trimethylsilyl ethers, Silylation, Hydroxyl group, 1’-(Ethane-1, 2-diyl)dipyridinium bistribromide, Desilylation,
ملخص المقالة :
1,1’-(Ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) was used as a chemoselective and effective organocatalyst for the silylation of hydroxyl groups as well as desilylation of trimethylsilyl ethers under mild conditions at room temperature with good to excellent yields.
[1] S.S. Kim, G. Rajagopal, Synth. Commun. 34 (2004) 2237-2243.
[2] D. Choudhary, S. Paul, R. Gupta, J.H. Clark, Green Chem. 8 (2006) 479-482.
[3] P. Ferreira, E. Phillips, D. Rippon, S.C. Tsang, Appl. Catal. B: Environ. 61 (2005) 206-211.
[4] M.A. Zolfigol, F. Shirini, G. Chehardoli, E. Kolvari, J. Mol. Catal. A: Chem. 265 (2006) 272-275.
[5] F.D. Cattaway, G. Hoyle, J. Chem. Soc. (1923) 654-662.
[6] M. Avramoff, J. Weiss, O. Schaechter, J. Org. Chem. 28 (1963) 3256-3258.
[7] S. Kajigneshi, T. Kakinami, H. Tokiyama, T. Hirakawa, T. Okamoto, Chem. Lett. (1987) 627-630.
[8] R.E. Buckles, A.I. Popov, W.F. Zelezny, R.J. Smith J. Am. Chem. Soc. 73 (1951) 4525-4528.
[9] H.A. Muathen, J. Org. Chem. 57 (1992) 2740-2741.
[10] L.F. Fieser, M. Fieser, Reagents for Organic Synthesis. New York: Wiley, 1967, 967.
[11] I.Yavari, A. Shaabani, J. Chem. Res. (S) (1994) 274-275.
[12] M.M. Heravi, F. Derikvand, M. Ghassemzadeh, B. Neümuller, Tetrahedron Lett. 46 (2005) 6243- 6245.
[13] W. Bao, Z. Wang, Green Chem. 8 (2006) 1028-1033.
[14] C. Chiappe, E. Leandri, D. Pieraccini, Chem. Commun. (2004) 2536-2537.
[15] M.K. Chaudhuri, A.T. Khan, B.K. Patel, Tetrahedron Lett. 39 (1998) 8163-8166.[16] M.A. Zolfigol, G. Chehardoli, S. Salehzadeh, H. Adams, M.D. Ward, Tetrahedron Lett. 48 (2007) 7969-7973.
[17] V. Kavala, S. Naik, B.K. Patel, J. Org. Chem. 70 (2005) 4267-4271.
[18] M.A. Zolfigol,G. Chehardoli, E. Ghaemi, E. Madrakian, R. Zare, T. Azadbakht, K. Niknam, S. Mallakpour, Monatsh. Chem. 139 (200.8) 261-265.
[19] E. Kolvari, A.G. Choghamarani, P. Salehi, F. Shirini, M.A. Zolfigol, J. Iran. Chem. Soc. 4 (2007) 126-174.
[20] M.A. Zolfigol, F. Shirini, G. Chehardoli, E. Kolvari, J. Mol. Catal. A: Chem. 265 (2006) 271-275.
[21] M.A. Zolfigol,M. Bagherzadeh, S. Mallakpour, G. Chehardoli, A. Ghorbani-Choghamarani,N. Koukabi, M. Dehghanian, M. Doroudgar J. Mol. Catal. A: Chem. 270 (2007) 219-224.
[22] M.A. Zolfigol, M. Bagherzadeh, S. Mallakpour, G. Chehardoli, E. Kolvari, A. Ghorbani-Choghamrani,N.Koukabi,Catal. Commun. 8 (2007) 256-260.
[23] K. Niknam, M.A. Zolfigol, G. Chehardoli, M. Dehghanian, Chin. J. Catal. 29 (200.8) 901-906 and references cited therein.
[24] D. Zareyee, B. Karimi, Tetrahedron Lett. 48 (2007) 1277-1280.
[25] A. Khazaei, M.A. Zolfigol, Z. Tanbakouchian, M. Shiri, K. Niknam, J. Saien, Catal. Commun. 8 (2007) 917–920.
[26] H. Firouzabadi, N. Iranpoor, S. Sobhani, S. Ghassamipour, J. Organomet. Chem. 689 (2004) 3197-3202.
[27] V.H. Tillu, V.H. Jadhav, H.B. Borate, R.D. Wakharkar, Arkivoc (2004) 83-88.
[28] B. Karimi, B. Golshani, J. Org. Chem. 65 (2000) 7228-7230.
[29] M.A. Zolfigol, I. Mohammadpoor-Baltork, M. Shiri, J. Iran. Chem. Soc., 5 (200.8) 90-95.
[30] A. Bamoniri, B.F. Mirjalili, M.A. Zolfigol, I. Mohammadpoor-Baltork, J. Iran. Chem. Soc., 4 (2007) 332-335.
[31] A. Bamoniri, M.A. Zolfigol, I. Mohammadpoor-Baltork, B.F. Mirjalili, J. Iran. Chem. Soc. 3 (2006) 85-88.
