F. Zadehahmadi et al.
References
[1] K. Jarowicki, P. Kocienski, J. Chem. Soc. Perkin Trans. 1998, 1,
4005–4037.
[2] G. Sartori, R. Ballini, F. Bigi, G. Bosica, R. Maggi, P. Righi, Chem. Rev. 2004,
104, 199–250.
[3] Z. H. Zhang, T. S. Li, F. Yang, C. G. Fu, Synth. Commun. 1998, 28,
3105–3114.
[4] M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati, U. Costantino, Synth.
Commun. 1999, 29, 541–546.
[5] B. Karimi, B. Golshani, J. Org. Chem. 2000, 65, 7228–7230.
[6] H. Firouzabadi, N. Iranpoor, K. Amani, F. Nowrouzi, J. Chem. Soc. Perkin
Trans. 2002, 1, 2601–2604.
[7] F. Shirini, M. Mamaghani, S. V. Atghia, Appl. Clay Sci. 2012, 58, 67–72.
[8] D. Zareyee, B. Karimi, Tetrahedron Lett. 2007, 48, 1277–1280.
[9] M.
Moghadam,
S.
Tangestaninejad,
V.
Mirkhani,
I. Mohammadpoor-Baltork, S. Chahardahcheric, Z. Tavakoli,
J. Organometal. Chem. 2008, 693, 2041–2046.
[10] H. Firouzabadi, N. Iranpoor, S. Farahi, Catal. Commun. 2009, 10,
1547–1550.
[11] M.
Moghadam,
S.
Tangestaninejad,
V.
Mirkhani,
I. Mohammadpoor-Baltork, S. Gharaati, Polyhedron 2010, 29, 212–219.
[12] F. Shirini, S. V. Atghia, M. G. Jirdehi, Catal. Commun. 2012, 18, 5–10.
[13] M. Yadegari, M. Moghadam, S. Tangestaninejad, V. Mirkhani,
I. Mohammadpoor-Baltork, Polyhedron 2012, 31, 332–338.
[14] M. Sridhar, J. Raveendra, B. China Ramanaiah, C. Narsaiah, Tetrahedron
Lett. 2011, 52, 5980–5982.
[15] F. Shirini, N. G. Khaligh, S. Akbari-Dadamahaleh, J. Mol. Catal. A 2012,
365, 15–23.
Figure 1. Diffuse reflectance UV–visible spectra of (A) [SnIV(TNH2PP)(OTf)2]/
[16] M. Torki, S. Tangestaninejad, V. Mirkhani, M. Moghadam,
I. Mohammadpoor-Baltork, Appl. Organometal. Chem. 2014, 28,
304–309.
CM-MIL-101 and (B) recovered catalyst.
[17] P. Villabrille, G. Romanelli, N. Quaranta, P. Vázquez, Appl. Catal. B 2010,
96, 379–386.
[18] F. Shirini, E. Mollarazi, Catal. Commun. 2007, 8, 1393–1396.
[19] G. Romanelli, D. Ruiz, P. Vázquez, H. Thomas, J. C. Autino, Chem. Eng. J.
2010, 161, 355–362.
[20] A. Rahmatpour, Polyhedron 2012, 44, 66–71.
[21] A. Khazaei, A. Rostami, M. Mahboubifar, Catal. Commun. 2007, 8,
383–388.
[22] T. S. Reddy, K. Ravinder, N. Suryakiran, M. Narasimhulu, K. C. Mahesh,
Y. Venkateswarlu, Tetrahedron Lett. 2006, 47, 2341–2344.
[23] M. M. Heravi, F. K. Behbahani, H. A. Oskooie, R. Hekmat Shoar,
Tetrahedron Lett. 2005, 46, 2543–2545.
[24] B. M. Choudary, V. Neeraja, M. Lakshmi Kantam, J. Mol. Catal. A 2001,
175, 169–172.
[25] J. H. Yang, X. Zhang, W. Y. Liu, Chin. Chem. Lett. 2008, 19, 893–896.
[26] G. Chehardoli, M. A. Zolfigol, F. Derakhshanpanah, Chin. J. Catal. 2013,
34, 1730–1733.
[27] G. P. Romanelli, J. C. Autino, M. N. Blanco, L. R. Pizzio, Appl. Catal. A
2005, 295, 209–215.
[28] G. Romanelli, P. Vázquez, L. Pizzio, N. Quaranta, J. Autino, M. Blanco,
C. Cáceres, Appl. Catal. A 2004, 261, 163–170.
[29] B. L. A. Prabhavathi Devi, K. N. Gangadhar, K. L. N. Siva Kumar,
K. Shiva Shanker, R. B. N. Prasad, P. S. Sai Prasad, J. Mol. Catal. A 2011,
345, 96–100.
Figure 2. FT-IR spectra of (A) [SnIV(TNH2PP)(OTf)2]/CM-MIL-101 and (B)
recovered catalyst.
[30] K. Tanemura, T. Suzuki, Tetrahedron Lett. 2013, 54, 6740–6743.
[31] D. B. G. Williams, S. B. Simelane, M. Lawton, H. H. Kinfe, Tetrahedron
2010, 66, 4573–4576.
[32] M. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chem. 1977, 42,
3772–3774.
[33] S. Ma, L. M. Venanzi, Tetrahedron Lett. 1993, 34, 5269–5272.
[34] M. H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork,
V. Mirkhani, B. Yadollahi, Tetrahedron Lett. 2001, 42, 2851–2853.
[35] K. Suda, M. Sashima, M. Izutsu, F. Hino, J. Chem. Soc. Chem. Commun.
1994, 949–950.
Conclusions
We have reported a rapid and efficient catalytic system for
trimethylsilylation and tetrahydropyranylation of alcohols and
phenols with HMDS and DHP, respectively. The results showed that
this system catalysed the protection of primary, secondary and
tertiary alcohols, as well as phenols in very short reaction times
and with high yields under mild conditions (room temperature).
Finally the catalyst could be reused several times without any
noticeable catalyst leaching.
[36] S. Tangestaninejad, V. Mirkhani, Synth. Commun. 1999, 29, 2079–2083.
[37] M.
Moghadam,
S.
Tangestaninejad,
V.
Mirkhani,
I. Mohammadpoor-Baltork, S. Gharaati, Compt. Rend. Chim. 2011,
14, 1080–1087.
[38] S. Gharaati, M. Moghadam, S. Tangestaninejad, V. Mirkhani,
Acknowledgement
I. Mohammadpoor-Baltork, Polyhedron 2012, 35, 87–95.
[39] M.
Moghadam,
S.
Tangestaninejad,
V.
Mirkhani,
The authors are grateful to the Research Council of the University of
Isfahan for financial support of this work.
I. Mohammadpoor-Baltork, M. Khajehzadeh, F. Kosari, M. Araghi,
Polyhedron 2010, 59, 238–243.
wileyonlinelibrary.com/journal/aoc
Copyright © 2015 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. (2015)