Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Simple and One-pot Oxidative Conversion of Alcohols or Aldehydes to the Nitriles using NaIO4/KI in Aqueous NH3

  • Received : 2011.08.30
  • Accepted : 2011.09.27
  • Published : 2011.12.20
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Abstract

Sodium periodate ($NaIO_4$) and potassium iodide (KI) in aqueous ammonia has been used for the one-pot synthesis of nitriles from the corresponding aldehydes and alcohols in moderate to good yield. This transformation, proceeds via an in situ oxidation- imination-aldimine oxidation sequence.

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References

  1. Bag, S.; Tawari, N. R.; Degani, M. S. Arkivoc 2009, (xiv), 118.
  2. Kim, M.; Lee, J.; Lee, H. Y.; Chang, S. Adv. Synth. Catal. 2009, 351, 1807. https://doi.org/10.1002/adsc.200900251
  3. Iida, S.; Ohmura, R.; Togo, H. Tetrahedron 2009, 65, 6257. https://doi.org/10.1016/j.tet.2009.05.001
  4. Leadbeater, N. E.; Torenius, H. M.; Tye, H. Tetrahedron 2003, 59, 2253. https://doi.org/10.1016/S0040-4020(03)00214-X
  5. Harrison, C.; Hodge, P.; Rogers, W. Synthesis 1977, 41.
  6. Yang, S. H.; Chang, S. Org. Lett. 2001, 3, 4209. https://doi.org/10.1021/ol0168768
  7. Chill, S. T.; Mebane, R. C. Synth. Commun. 2009, 39, 3601. https://doi.org/10.1080/00397910902788174
  8. Movassagh, B.; Shokri, S. Tetrahedron Lett. 2005, 46, 6923. https://doi.org/10.1016/j.tetlet.2005.08.007
  9. Maeyama, K.; Kobayashi, M.; Kato, H.; Yonezawa, N. Synth. Commun. 2002, 32, 2519. https://doi.org/10.1081/SCC-120005932
  10. Cho, B. R.; Chung, H. S.; Cho, N. S. J. Org. Chem. 1998, 63, 4685. https://doi.org/10.1021/jo980264s
  11. Iranpoor, N.; Firouzabadi, H.; Akhlaghinia, B.; Nowrouzi, N. J. Org. Chem. 2004, 69, 2562. https://doi.org/10.1021/jo035238v
  12. Carmeli, M.; Shefer, N.; Rozen, S. Tetrahedron Lett. 2006, 47, 8969. https://doi.org/10.1016/j.tetlet.2006.10.014
  13. Talukdar, S.; Hsu, J. L.; Chou, T. C.; Fang, J. M. Tetrahedron Lett. 2001, 42, 1103. https://doi.org/10.1016/S0040-4039(00)02195-X
  14. Stevens, T. E. J. Org. Chem. 1961, 26, 2531. https://doi.org/10.1021/jo01351a603
  15. Reddy, K. R.; Maheswari, C. U.; Venkateshwar, M.; Prashanthi, S.; Kantam, M. L. Tetrahedron Lett. 2009, 50, 2050. https://doi.org/10.1016/j.tetlet.2009.02.057
  16. Parameswaram, K. N.; Friedman, O. M. Chem. Ind. (London) 1965, 988.
  17. Mori, N.; Togo, H. Synlett 2005, 1964.
  18. Bandgar, B. P.; Makone, S. S. Synth. Commun. 2006, 36, 1347. https://doi.org/10.1080/00397910500522009
  19. Arote, N. D.; Bhalerao, D. S.; Akamanchi, K. G. Tetrahedron Lett. 2007, 48, 3651. https://doi.org/10.1016/j.tetlet.2007.03.137
  20. Movassagh, B.; Fazeli, A. Synthetic Commun. 2007, 37, 623. https://doi.org/10.1080/00397910601055198
  21. Dewan, S. K.; Singh, R.; Kumar, A. Synthetic Commun. 2004, 34, 2025. https://doi.org/10.1081/SCC-120037915
  22. Iida, S.; Togo, H. Tetrahedron 2007, 63, 8274. https://doi.org/10.1016/j.tet.2007.05.106
  23. Chen, F. E.; Li, Y. Y.; Xu, M.; Jia, H. Q. Synthesis 2002, 1804.
  24. http://www.chemblink.com/products/4210-32-6.html.
  25. http://www.chemexper.com/chemicals/supplier/cas/78-82-0.html.
  26. Sharghi, H.; Sarvari, M. H. Tetrahedron 2002, 58, 10323. https://doi.org/10.1016/S0040-4020(02)01417-5

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