Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Received : 2012.02.29
  • Accepted : 2012.03.26
  • Published : 2012.07.20
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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.

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References

  1. Shabani, A.; Lee, D. G. Tetrahedron Lett. 2001, 42, 5833-5836. https://doi.org/10.1016/S0040-4039(01)01129-7
  2. Mirjalili, F.; Zolfigol, M. A.; Bamoniri, A.; Zarei, A. Bull. Korean Chem. Soc. 2003, 24, 400-402. https://doi.org/10.5012/bkcs.2003.24.3.400
  3. Matsubara, J.; Nakao, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1992, 33, 4187-4190. https://doi.org/10.1016/S0040-4039(00)74685-5
  4. Aoyama, T.; Sonoda, N.; Yamauchi, M.; Toriyama, K.; Anzai, M.; Ando, A.; Shioiri, T. Synlett 1998, 35-36.
  5. Struve, G.; Seltzer, S. J. Org. Chem. 1982, 47, 2109- 2113. https://doi.org/10.1021/jo00132a023
  6. Lou, J. D.; Xu, Z. N. Tetrahedron Lett. 2002, 43, 6149- 6150. https://doi.org/10.1016/S0040-4039(02)01345-X
  7. Lou, J. D.; Xu, Z. N. Tetrahedron Lett. 2002, 43, 8843-8844. https://doi.org/10.1016/S0040-4039(02)02234-7
  8. Mirjalili, F.; Zolfigol, M. A.; Bamoniri, A.; Zarei, A. Phosphorus Sulfur and Silicon 2003, 178, 1845-1849. https://doi.org/10.1080/10426500307835
  9. Hajipour, A. R.; Mallakpour, S.; Khoee, S. Synlett 2000, 740-742.
  10. Cardillo, G.; Orena, M.; Sandri, S. Synthesis 1976, 394-396.
  11. Gasparrini, F.; Giovannoli, M.; Misiti, D.; Natile, G.; Palmieri, G. Synth. Commun. 1988, 18, 69-75. https://doi.org/10.1080/00397918808057821
  12. Strazzolini, P.; Runcio, A. Eur. J. Org. Chem. 2003, 526-536.
  13. Barrett, A. G. M.; Braddock, D. C.; McKinnell, R. M.; Waller, F. J. Synlett 1999, 1489-1490.
  14. Minisci, F.; Porta, O.; Recupero, F.; Punta, C.; Gambarotti, C.; Pierini, M.; Galimberti, L. Synlett 2004, 2203-2205.
  15. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. https://doi.org/10.1021/cr010003+
  16. Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656-3665. https://doi.org/10.1002/anie.200500115
  17. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287. https://doi.org/10.1021/ja00019a027
  18. More, J. D.; Finney, N. S. Org. Lett. 2002, 4, 3001-3003. https://doi.org/10.1021/ol026427n
  19. Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 2058-2059. https://doi.org/10.1021/jo026751w
  20. Muncusco, A. J.; Huang, S. L.; Swern, D. J. J. Org. Chem. 1978, 43, 2480-2482. https://doi.org/10.1021/jo00406a041
  21. Tidwell, T. T. Synthesis 1990, 857-870.
  22. Sharma, V. B.; Jain, S. L.; Sain, B. Synlett 2005, 173-175.
  23. Bogda, D.; Lukasiewicz, M. Synlett 2000, 143-145.
  24. Chhikara, B. S.; Chandra, R.; Tandon, V. Synlett 2005, 872-874.
  25. Liu, C.; Han, J.; Wang, J. Synlett 2007, 643-645.
  26. Ferguson, G.; Ajjou, A. N. Tetrahedron Lett. 2003, 44, 9139-9142. https://doi.org/10.1016/j.tetlet.2003.10.052
  27. Zolfigol, M. A.; Shirini, F.; Ghorbani Choghamaran, A. Synthesis 2006, 2043-2046.
  28. Mirafzal, G. A.; Lozeva, A. M. Tetrahedron Lett. 1998, 39, 7263-7266. https://doi.org/10.1016/S0040-4039(98)01584-6
  29. Hanessian, S.; Wong, D. H.; Therien, M. Synthesis 1981, 394-396.
  30. Arterburn, J. B. Tetrahedron 2001, 57, 9765-9788. https://doi.org/10.1016/S0040-4020(01)01009-2
  31. Wu, S.; Ma, H.; Lei, Z. Synlett 2010, 2818-2822.
  32. Malik, P.; Chakraborty, D. Synthesis 2010, 3736-3740.
  33. Prasanna, T. S. R.; Mohanaraju, K. Tetrahedron Lett. 2011, 52, 6971-6973. https://doi.org/10.1016/j.tetlet.2011.10.086
  34. Bandna, Aggarwal, N.; Das, P. Tetrahedron Lett. 2011, 52, 4954- 4956. https://doi.org/10.1016/j.tetlet.2011.07.073
  35. Tsuchiya, D.; Moriyama, K.; Togo, H. Synlett 2011, 2701-2704.
  36. Dewan, A.; Sarma, T.; Bora, U.; Kakati, D. K Tetrahedron Lett. 2011, 52, 2563-2565. https://doi.org/10.1016/j.tetlet.2011.03.044
  37. Moyer, S. A. Funk, T. W. K Tetrahedron Lett. 2010, 51, 5430-5433. https://doi.org/10.1016/j.tetlet.2010.08.004
  38. Hirano, M.; Ukawa, K.; Yakabe, S.; Morimoto, T. Synth. Commun. 1997, 27, 1527-1533. https://doi.org/10.1080/00397919708006089
  39. Hirano, M.; Komiya, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Org. Prep. Proced. Int. 1996, 28, 705-708. https://doi.org/10.1080/00304949609356737
  40. Hirano, M.; Ukawa, K.; Yakabe, S.; Morimoto, T. Org. Prep. Proced. Int. 1997, 29, 480-484. https://doi.org/10.1080/00304949709355223
  41. Khadilkar, B.; Borkar, S. Synth. Commun. 1998, 28, 207-212. https://doi.org/10.1080/00397919808005712
  42. Hirano, M.; Komiya, K.; Morimito, T. Org. Prep. Proced. Int. 1995, 27, 703-706. https://doi.org/10.1080/00304949509458538
  43. Heravi, M. M.; Ajami, D.; Mojtahedi, M. M.; Ghassemzadeh, M. Tetrahedron Lett. 1999, 40, 561-562. https://doi.org/10.1016/S0040-4039(98)02355-7
  44. Varma, R. S.; Dahiya, R. Tetrahedron Lett. 1998, 39, 1307-1308. https://doi.org/10.1016/S0040-4039(97)10763-8
  45. Laszlo, P.; Cornelis, A. Synthesis 1985, 909-918.
  46. Laszlo, P.; Cornelis, A. Synthesis 1980, 849-850.
  47. Heravi, M. M.; Ajami, D.; Mojtahedi, M. M.; Ghassemzadeh, M. Chem. Commun. 1999, 833-834.
  48. Firouzabadi, H.; Iranpoor, N.; Amani, K. Synthesis 2003, 849- 412.
  49. Lee, J. C.; Lee, J. Y.; Lee, J. M. Bull. Korean Chem. Soc. 2005, 26, 1300-1302. https://doi.org/10.5012/bkcs.2005.26.8.1300
  50. Oda, Y.; Hirano, K.; Satoh, T.; Kuwabata, S.; Miura, M. Tetrahedron Lett. 2011, 52, 5392-5394. https://doi.org/10.1016/j.tetlet.2011.08.053
  51. Zolfigol, M. A. Tetrahedron 2001, 57, 9509-9511. https://doi.org/10.1016/S0040-4020(01)00960-7
  52. Zolfigol, M. A.; Shirini, F.; Ghorbani Choghamarani, A.; Mohammadpoor- Baltork, I. Green Chem. 2002, 4, 562-564. https://doi.org/10.1039/b208328k
  53. Hajipour, A. R.; Mirjalili, B. B. F.; Zarei, A.; Khazdooz, L.; Ruoho, A. E. Tetrahedron Lett. 2004, 45, 6607-6609. https://doi.org/10.1016/j.tetlet.2004.07.023
  54. 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. https://doi.org/10.5012/bkcs.2004.25.9.1414
  55. Hajipour, A. R.; Zarei, A.; Khazdooz, L.; Mirjalili, B. B. F.; Sheikhan, N.; Zahmatkesh, S.; Ruoho, A. E. Synthesis 2005, 3644-3648.
  56. Hajipour, A. R.; Zarei, A.; Ruoho, A. E. Ruoho Synth. Commun. 2006, 36, 1039-1050. https://doi.org/10.1080/00397910500503421
  57. Hajipour, A. R.; Zarei, A.; Khazdooz, L.; Ruoho, A. E. Synth. Commun. 2005, 35, 2237- 2241. https://doi.org/10.1080/00397910500184685
  58. Hajipour, A. R.; Khazdooz, L.; Ruoho, A. E. Catal. Commun. 2008, 9, 89-96. https://doi.org/10.1016/j.catcom.2007.05.003
  59. Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994.
  60. Smith, M. B.; March, J. Advanced Organic Chemistry; Wiley and Sons: New York, 2001; p 327-351.
  61. Hajipour, A. R.; Rafiee, F.; Ruoho, A. E. Synlett 2007, 1118-1120.
  62. Matsumura, Y.; Yamamoto, Y.; Moriyama, N.; Furukubo, S.; Iwasaki, F.; Onomura, O. Tetrahedron Lett. 2004, 45, 8221-8224. https://doi.org/10.1016/j.tetlet.2004.09.037

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