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http://dx.doi.org/10.5012/bkcs.2012.33.7.2149

Metal-Free Oxidation of Alcohols to Their Corresponding Carbonyl Compounds Using NH4NO3/Silica Sulfuric Acid  

Zarei, Amin (Department of Science, Fasa Branch, Islamic Azad University)
Publication Information
Abstract
A metal-free and efficient procedure for the oxidation of alcohols into the corresponding carbonyl compounds has been described using ammonium nitrate in the presence of silica sulfuric acid under mild and heterogeneous conditions. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are among the advantages of this method.
Keywords
Oxidation; Alcohols; Ammonium nitrate; Silica sulfuric acid;
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1 Hirano, M.; Komiya, K.; Morimito, T. Org. Prep. Proced. Int. 1995, 27, 703-706.   DOI
2 Heravi, M. M.; Ajami, D.; Mojtahedi, M. M.; Ghassemzadeh, M. Tetrahedron Lett. 1999, 40, 561-562.   DOI
3 Varma, R. S.; Dahiya, R. Tetrahedron Lett. 1998, 39, 1307-1308.   DOI
4 Laszlo, P.; Cornelis, A. Synthesis 1985, 909-918.
5 Laszlo, P.; Cornelis, A. Synthesis 1980, 849-850.
6 Hanessian, S.; Wong, D. H.; Therien, M. Synthesis 1981, 394-396.
7 Arterburn, J. B. Tetrahedron 2001, 57, 9765-9788.   DOI
8 Wu, S.; Ma, H.; Lei, Z. Synlett 2010, 2818-2822.
9 Malik, P.; Chakraborty, D. Synthesis 2010, 3736-3740.
10 Prasanna, T. S. R.; Mohanaraju, K. Tetrahedron Lett. 2011, 52, 6971-6973.   DOI
11 Bandna, Aggarwal, N.; Das, P. Tetrahedron Lett. 2011, 52, 4954- 4956.   DOI
12 Tsuchiya, D.; Moriyama, K.; Togo, H. Synlett 2011, 2701-2704.
13 Dewan, A.; Sarma, T.; Bora, U.; Kakati, D. K Tetrahedron Lett. 2011, 52, 2563-2565.   DOI
14 Liu, C.; Han, J.; Wang, J. Synlett 2007, 643-645.
15 Moyer, S. A. Funk, T. W. K Tetrahedron Lett. 2010, 51, 5430-5433.   DOI
16 Hirano, M.; Ukawa, K.; Yakabe, S.; Morimoto, T. Synth. Commun. 1997, 27, 1527-1533.   DOI
17 Hirano, M.; Komiya, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Org. Prep. Proced. Int. 1996, 28, 705-708.   DOI
18 Hirano, M.; Ukawa, K.; Yakabe, S.; Morimoto, T. Org. Prep. Proced. Int. 1997, 29, 480-484.   DOI
19 Khadilkar, B.; Borkar, S. Synth. Commun. 1998, 28, 207-212.   DOI
20 Lou, J. D.; Xu, Z. N. Tetrahedron Lett. 2002, 43, 8843-8844.   DOI
21 Mirjalili, F.; Zolfigol, M. A.; Bamoniri, A.; Zarei, A. Phosphorus Sulfur and Silicon 2003, 178, 1845-1849.   DOI
22 Hajipour, A. R.; Rafiee, F.; Ruoho, A. E. Synlett 2007, 1118-1120.
23 Hajipour, A. R.; Khazdooz, L.; Ruoho, A. E. Catal. Commun. 2008, 9, 89-96.   DOI
24 Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994.
25 Smith, M. B.; March, J. Advanced Organic Chemistry; Wiley and Sons: New York, 2001; p 327-351.
26 Matsumura, Y.; Yamamoto, Y.; Moriyama, N.; Furukubo, S.; Iwasaki, F.; Onomura, O. Tetrahedron Lett. 2004, 45, 8221-8224.   DOI
27 Oda, Y.; Hirano, K.; Satoh, T.; Kuwabata, S.; Miura, M. Tetrahedron Lett. 2011, 52, 5392-5394.   DOI
28 Heravi, M. M.; Ajami, D.; Mojtahedi, M. M.; Ghassemzadeh, M. Chem. Commun. 1999, 833-834.
29 Firouzabadi, H.; Iranpoor, N.; Amani, K. Synthesis 2003, 849- 412.
30 Lee, J. C.; Lee, J. Y.; Lee, J. M. Bull. Korean Chem. Soc. 2005, 26, 1300-1302.   DOI
31 Zolfigol, M. A. Tetrahedron 2001, 57, 9509-9511.   DOI
32 Zolfigol, M. A.; Shirini, F.; Ghorbani Choghamarani, A.; Mohammadpoor- Baltork, I. Green Chem. 2002, 4, 562-564.   DOI
33 Hajipour, A. R.; Mirjalili, B. B. F.; Zarei, A.; Khazdooz, L.; Ruoho, A. E. Tetrahedron Lett. 2004, 45, 6607-6609.   DOI
34 Zolfigol, M. A.; Mirjalili, B. B. F.; Bamoniri, A.; Karimi, M. A.; Zarei, A.; Khazdooz, L.; Noei, J. Bull. Korean Chem. Soc. 2004, 25, 1414-1416.   DOI
35 Hajipour, A. R.; Zarei, A.; Khazdooz, L.; Mirjalili, B. B. F.; Sheikhan, N.; Zahmatkesh, S.; Ruoho, A. E. Synthesis 2005, 3644-3648.
36 Hajipour, A. R.; Zarei, A.; Ruoho, A. E. Ruoho Synth. Commun. 2006, 36, 1039-1050.   DOI
37 Hajipour, A. R.; Zarei, A.; Khazdooz, L.; Ruoho, A. E. Synth. Commun. 2005, 35, 2237- 2241.   DOI
38 Ferguson, G.; Ajjou, A. N. Tetrahedron Lett. 2003, 44, 9139-9142.   DOI
39 Zolfigol, M. A.; Shirini, F.; Ghorbani Choghamaran, A. Synthesis 2006, 2043-2046.
40 Mirafzal, G. A.; Lozeva, A. M. Tetrahedron Lett. 1998, 39, 7263-7266.   DOI
41 Strazzolini, P.; Runcio, A. Eur. J. Org. Chem. 2003, 526-536.
42 Hajipour, A. R.; Mallakpour, S.; Khoee, S. Synlett 2000, 740-742.
43 Cardillo, G.; Orena, M.; Sandri, S. Synthesis 1976, 394-396.
44 Gasparrini, F.; Giovannoli, M.; Misiti, D.; Natile, G.; Palmieri, G. Synth. Commun. 1988, 18, 69-75.   DOI
45 Barrett, A. G. M.; Braddock, D. C.; McKinnell, R. M.; Waller, F. J. Synlett 1999, 1489-1490.
46 Minisci, F.; Porta, O.; Recupero, F.; Punta, C.; Gambarotti, C.; Pierini, M.; Galimberti, L. Synlett 2004, 2203-2205.
47 Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.   DOI
48 Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656-3665.   DOI
49 Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.   DOI
50 More, J. D.; Finney, N. S. Org. Lett. 2002, 4, 3001-3003.   DOI
51 Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 2058-2059.   DOI
52 Muncusco, A. J.; Huang, S. L.; Swern, D. J. J. Org. Chem. 1978, 43, 2480-2482.   DOI
53 Tidwell, T. T. Synthesis 1990, 857-870.
54 Sharma, V. B.; Jain, S. L.; Sain, B. Synlett 2005, 173-175.
55 Bogda, D.; Lukasiewicz, M. Synlett 2000, 143-145.
56 Chhikara, B. S.; Chandra, R.; Tandon, V. Synlett 2005, 872-874.
57 Aoyama, T.; Sonoda, N.; Yamauchi, M.; Toriyama, K.; Anzai, M.; Ando, A.; Shioiri, T. Synlett 1998, 35-36.
58 Shabani, A.; Lee, D. G. Tetrahedron Lett. 2001, 42, 5833-5836.   DOI   ScienceOn
59 Mirjalili, F.; Zolfigol, M. A.; Bamoniri, A.; Zarei, A. Bull. Korean Chem. Soc. 2003, 24, 400-402.   DOI
60 Matsubara, J.; Nakao, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1992, 33, 4187-4190.   DOI
61 Struve, G.; Seltzer, S. J. Org. Chem. 1982, 47, 2109- 2113.   DOI
62 Lou, J. D.; Xu, Z. N. Tetrahedron Lett. 2002, 43, 6149- 6150.   DOI