22
F. Shirini et al. / Journal of Molecular Catalysis A: Chemical 365 (2012) 15–23
Table 4
Comparison of the silylation of benzhydrol and triphenyl methanol in the presence of [Dsim]HSO4 with some other catalysts.
Entry
Catalyst/solvent/condition
Benzhydrol
Time (min)
Triphenyl methanol
Time (min)
Refs.
Yield (%)
Yield (%)a
1
2
3
4
5
6
7
8
TCCA (10 mol%)/CH2Cl2/r.t.
H3PW12O40 (1 mol%)/neat/55–60 ◦
LiClO4 SiO2 (100 mg)/CH2Cl2/r.t.
Mg(OTf)2 (1 mol%)/neat/r.t.
ZrCl4 (2 mol%)/CH3CN/r.t.
V(HSO4)3(3.0 mol%)/CH3CN/r.t.
Fe(HSO4)3 (25 mol%)/CH3CN/r.t.
Fe(HSO4)3 (25 mol%)/neat/r.t.
TiCl3(OTf) (1 mol%)/neat/r.t.
SaSA (10 mol%)/CH3CN/r.t.
SuSA (2 mol%)/CH3CN/r.t.
180
48
50
120
2
95
93
87
70
90
93
75
85
92
92
96
87
98
96
98
–
–
–
–
8
–
–
–
–
–
–
–
–
–
4
–
–
–
–
82
–
–
–
–
–
[28]
[32]
[39]
[41]
[44]
[52]
[53]
[53]
[55]
[57]
[58]
[59]
[60]
[61]
This work
C
5
50
42
2
10
1
5
50
1
9
10
11
12
13
14
15
–
–
–
–
SANM (20 mg)/CH3CN/r.t.
P(4-VP) (10 mg)/CH3CN/r.t.
[Msim]HSO4 (2 mol%)/neat/r.t.
[Dsim]HSO4 (2 mol%)/neat/r.t.
1
98
a
Isolated yield.
Fig. 4. Reusability of [Dsim]HSO4.
4. Conclusion
[11] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Org. Prep. Proced. Int. 42
(2010) 95–102.
[12] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Scientia Iranica: Trans C:
Chem. Chem. Eng. 17 (2010) 31–36.
[13] C.-X. Miao, L.-N. He, J.-Q. Wang, J.-L. Wang, Adv. Synth. Catal. 351 (2009)
2209–2216.
[14] A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes Jr., J.H. Davis, J.
Am. Chem. Soc. 124 (2002) 5962–5963.
[15] A. Arfan, J.P. Bazureau, Org. Process Res. Dev. 9 (2005) 743–748.
[16] P. Wasserscheid, M. Sesing, W. Korth, Green Chem. 4 (2002) 134–138.
[17] (a) P. Wasserscheid, R. van Hal, A. Bösmann, Green Chem. 4 (2002) 400–404;
(b) J. Fraga-Dubreuil, K. Bourahla, M. Rahmouni, J.P. Bazureau, J. Hamelin, Catal.
Commun. 3 (2002) 185–190;
In conclusion, here we have reported the preparation of 1,3-
disulfonic acid imidazolium hydrogen sulfate and its application
in the promotion of the silylation of alcohols and phenols with
HMDS and deprotection of the obtained trimethylsilanes. Mildness
of the reaction conditions, short reaction times, excellent yields,
easy work-up, halogen-free, recoverability and reusability of the
ionic liquid, and chemoselectivity are noteworthy advantages of
this method.
(c) M.T. Garcia, N. Gathergood, P.J. Scammells, Green Chem. 7 (2005) 9–14.
[18] N. Gathergood, M.T. Garcia, P.J. Scammells, Green Chem. 6 (2004) 166–175.
[19] G. Sartori, R. Ballani, F. Bigi, G. Bosica, R. Maggi, P. Righi, Chem. Rev. 104 (2004)
199–250.
Acknowledgment
[20] P.G.M. Wuts, T.W. Greene, Greene’s Protective Groups in Organic Synthesis,
fourth ed., John Wiley and Sons Inc., Hoboken, NJ, 2007.
[21] E.J. Corey, A. Venkateswarlu, J. Am. Chem. Soc. 94 (1972) 6190–6191.
[22] S.K. Chaudhary, O. Hernandez, Tetrahedron Lett. 20 (1979) 99–102.
[23] L. Lombardo, Tetrahedron Lett. 25 (1984) 227–228.
[24] G.A. Olah, B.G.B. Gupta, S.C. Narang, R. Malhorta, J. Org. Chem. 44 (1979)
4272–4275.
[25] B.A. D’Sa, D. McLeod, J.G. Verkade, J. Org. Chem. 62 (1997) 5057–5061.
[26] M. Suzuki, Tetrahedron 37 (1981) 3899–3910.
[27] C.A. Bruynes, T.K. Jurriens, J. Org. Chem. 47 (1982) 3966–3969.
[28] A. Khazaei, M.A. Zolfigol, A. Rostami, A. Ghobani Choghamarani, Catal. Commun.
8 (2007) 543–547.
[29] M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, U. Costantino, Synth. Commun.
29 (1999) 541–546.
[30] H. Firouzabadi, B. Karimi, Synth. Commun. 23 (1993) 1633–1641.
[31] B.P. Bandgar, P.P. Wadgaonkar, Synth. Commun. 27 (1997) 2069–2074.
[32] H. Firouzabadi, N. Iranpoor, K. Amani, F. Nowrouzi, J. Chem. Soc., Perkin Trans.
I (2002) 2601–2604.
[33] Z.H. Zhang, T.S. Li, F. Yang, C.G. Fu, Synth. Commun. 28 (1998) 3105–3114.
[34] B. Karimi, B. Golshani, J. Org. Chem. 65 (2000) 7228–7230.
[35] N. Azizi, M.R. Saidi, Organometallics 23 (2004) 1457–1458.
The authors are thankful to the Guilan University Research
Council for the partial support of this work.
References
[1] R.D. Rogers, K.R. Seddon (Eds.), Ionic Liquids: Industrial Applications to Green
Chemistry, American Chemical Society, Washington, DC, 2002.
[2] V.I. Parvulescu, C. Hardacre, Chem. Rev. 107 (2007) 2615–2665.
[3] M.J. Earle, S.P. Katdare, K.R. Seddon, Org. Lett. 6 (2004) 707–710.
[4] B.C. Ranu, S. Banerjee, J. Org. Chem. 70 (2005) 4517–4519.
[5] B.C. Ranu, L. Adak, S. Banerjee, Can. J. Chem. 85 (2007) 366–371.
[6] D. Saha, A. Saha, B.C. Ranu, Tetrahedron Lett. 50 (2009) 6088–6091.
[7] A. Zare, A.R. Moosavi-Zare, A. Hasaninejad, A. Parhami, A. Khalafi-Nezhad, M.H.
Beyzavi, Synth. Commun. 39 (2009) 3156–3165.
[8] A. Zare, A. Parhami, A.R. Moosavi-Zare, A. Hasaninejad, A. Khalafi-Nezhad, M.H.
Beyzavi, Can. J. Chem. 87 (2009) 416–421.
[9] A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri Rad, J. Comb. Chem. 12 (2010)
844–849.
[10] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, J. Iran. Chem. Soc. 7 (2010)
646–651.