Rice husk ash (RHA): A Highly efficient solid acid catalyst for the oxidation of alcohols and trimethylsilyl, tetrahydropyranyl and methoxymethyl ethers with CrO3

Iranian Journal of Catalysis

مقاله 4، دوره 5، شماره 3، آذر 2015، صفحه 223-230   

نوع مقاله: Short Communications

نویسندگان

Farhad Shirini^* ؛ Masoumeh Abedini؛ Mahnaz Shamsi-Sani؛ Mohadeseh Seddighi

Department of Chemistry, College of Science, University of Guilan, Rasht, Zip code 41335, I.R. Iran

چکیده

A mild, efficient and fast method for the oxidation of alcohols and trimethylsilyl, tetrahydropyranyl and methoxymethyl ethers to their corresponding carbonyl compounds using CrO3 in the presence of rice husk ash (RHA) is reported. All reactions were performed at room temperature in high to excellent yields. A new, efficient and green catalyst, heterogeneous reaction conditions, easy work-up of the products and high reaction rates are the main advantages of this method.

کلیدواژه‌ها

Rice Husk Ash؛ CrO3؛ Alcohols؛ Trimethylsilyl ethers؛ Tetrahydropyranyl ethers؛ Methoxymethyl ethers؛ Oxidation reactions

مراجع

[1] T. Fey, H. Fischer, S. Bachmann, K. Albert, C. Bolm, J. Org. Chem. 66 (2001) 8154-8159.
[2] E.J. Parish, S.A. Kizito, R. Heidepriem, Synth. Commun. 23 (1993) 223-230.
[3] H. Firouzabadi, I. Mohammadpoor-Baltork, Synth. Commun. 24 (1994) 1065-1077.
[4] H. Firouzabadi, F. Shirini, Synth. Commun. 26 (1996) 423-432.
[5] H. Firouzabadi, F. Shirini, Synth. Commun. 26 (1996) 649-655.
[6] J. Muzart, Synthesis (1993) 11-27.
[7] A.R. Hajipour, S.E. Mallakpour, I. Mohammadpoor-Baltork, M. Malakoutikhah, Tetrahedron. 58 (2002) 143-146.
[8] M.M. Hashemi, Y. Ahmadibeni, Monatsh. Chem. 134 (2003) 411-418.
[9] A.R. Hajipour, M. Mostafavi, A.E. Ruoho, Catal. Commun. 8 (2007) 1825-1828.
[10] M. Tajbakhsh, M.M. Lakouraj, A. Fadavi, Synth. Commun. 34 (2004) 1173-1182.
[11] P. Karthikeyan, S. Arunrao Aswar, P. Narayan Muskawar, P. Rambhau Bhagat, S.S. Kumar, Catal. Commun. 26 (2012) 189-193.
[12] H. Atashin, R. Malakooti, J. Saudi Chem. Soc. (2013) doi.org/10.1016/j.jscs.2013.09.007.
[13] H. Zhao, L. Zeng, Y. Li, C. Liu, B. Hou, D. Wub, N. Feng, A. Zheng, X. Xie, S. Su, N. Yu, Microporous Mesoporous Mater. 172 (2013) 67-76.
[14] X. Huang, X. Wang, M. Tan, X. Zou, W. Ding, X. Lu, Appl. Catal. A: Gen. 467 (2013) 407-413.
[15] H. Anderson, H. Uh, Synth. Commun. 3 (1973) 115-123.
[16] S. Filippo, C.I. Chern, J. Org. Chem. 42 (1977) 2182-2183.
[17] G. Cainell, G. Cardillo, M. Orena, S. Sandri, J. Am. Chem. Soc. 98 (1976) 6737-6738.
[18] J.M. Lalancette, G. Rollin, P. Dumas, Can. J. Chem. 50 (1972) 3058-3062.
[19] J.M. Aizpuruan, C. Palomo, Tetrahedron Lett. 24 (1983) 4367-4370.
[20] J. D. Lou, Y. Y. Wu, Synth. Commun. 17 (1987) 1717-1720.
[21] E. Santaniello, F. Ponti, A. Manzocchi, Synthesis (1978) 534-535.
[22] J. D. Lou, Synth. Commun. 19 (1989) 1841-1845.
[23] M.M. Heravi, D. Ajami, K. TabarHydar, M. Ghassemzadeh, J. Chem. Res. (1999) 334-335.
[24] Y.S. Cheng, W.L. Liu, S.H. Chen, Synthesis (1980) 223-225.
[25] H. Nakamura, H. Matsuhashi, Bull. Chem. Soc. Jpn. 68 (1995) 997-1000.
[26] L.H. Huang, J.D. Lou, L.H. Zhu, L. Ping, Y.B. Fu, Molecules 10 (2005) 794-799.
[27] A.R. Kiasat, F. Kazemi, K. Nourbakhsh, Indian J. Chem. 44 B (2005) 1524-1526.
[28] R.S. Varma, R.K. Saini, Tetrahedron Lett. 39 (1998) 1481-1482.
[29] G. Zhou, Z. Zhang, X. Feng, B. Dang, X. Li, Y. Sun, Catal. Commun. 25 (2012) 69-73.
[30] C.M. Granadeiro, P. Silva, V.K. Saini, F.A. Almeida Paz, J. Pires, L. Cunha-Silva, S.S. Balula, Catal. Today 218-219 (2013) 35-42.
[31] A.S. Burange, R.V. Jayaram, R. Shukla, A.K. Tyagi, Catal. Commun. 40 (2013) 27-31.
[32] F. Shirini, S. Akbari-Dadamahaleh, A. Mohammad-Khah, J. Mol. Catal. A: Chem. 363- 364 (2012) 10-17.
[33] F. Shirini, S. Akbari-Dadamahaleh, A. Mohammad-Khah, A.R. Aliakbar, C. R. Chimie. 16 (2013) 207-216.
[34] F. Shirini, S. Akbari-Dadamahaleh, A. Mohammad-Khah, C. R. Chimie. 16 (2013) 945-955.
[35] F. Shirini, M. Mamaghani, M. Seddighi, M. Catal. Commun. 36 (2013) 31-37.
[36] F. Shirini, M. A. Zolfigol, M. Khaleghi, Bull. Korean Chem. Soc. 24 (2003) 1021-1022.
[37] F. Shirini, M. A. Zolfigol, S. Torabi, Synth. Commun. 36 (2006) 2833-2840.
[38] F. Shirini, M. Esm-Hosseini, Z. Hejazi, J. Chem. Res. (2006) 29-33.
[39] F. Shirini, M.A. Zolfigol, M. Abedini, Scientia Iranica, 15 (2008) 440-443.
[40] F. Shirini, M.R. Yazdanbakhsh, M. Mahdavi Pop-Kiadeh, M. Abedini, J. Chem. Res. (2008) 409-419.
[41] F. Shirini, M. Khademian, M. Abedini, Arkivoc XV (2008) 71-78.
[42] F. Shirini, M. Abedini, A. Pourvali, Chin. Chem. Lett. 22 (2011) 33-36.
[43] F. Shirini, S. Saeidi, Chin. Chem. Lett. 19 (2008) 676-680.
[44] A.R. Pourali, M. Tabaean, S.M.R. Nazifi, Chin. Chem. Lett. 23 (2012) 21-24
[45] P. Sadeghzadeh, Ms. C. Thesis, University of Guilan (2011).
[46] F. Shirini, M. Abedini, A. Nasiri Abkenar, B. Baghernejad, Iran. J. Catal. 4 (2014) 1-7.