Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Mild and Efficient Silylcyanation of Aldehydes Catalyzed by Zirconium Complex

  • Published : 2005.02.20
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Abstract

An efficient method of addition of trimethylsilyl cyanide to aldehydes by employing a zirconium complex as the catalyst has been described. A variety of aromatic, aliphatic, cyclic and heterocyclic aldehydes has been converted into corresponding trimethylsilyl ethers in excellent yield within short reaction time.

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References

  1. Gregory., R. J. H. Chem. Rev. 1999, 99, 3649 https://doi.org/10.1021/cr9902906
  2. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer: Berlin, 1983; pp 6-20
  3. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989
  4. Evans, D. A.; Truesdake, L. K.; Carroll, G. L. J. Chem. Soc. 1973, 2, 55
  5. Lidy, W.; Sundermeyer, W. Tetrahedron Lett. 1973, 9, 1449
  6. Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 4, 537
  7. Lidy, W.; Sundermeyer, W. Chem. Ber. 1973, 106, 587 https://doi.org/10.1002/cber.19731060224
  8. Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 2525 https://doi.org/10.1016/0040-4039(96)00386-3
  9. Saravanan, P.; Vijaya, R.; Singh, V. K. Tetrahedron Lett. 1998, 39, 3823 https://doi.org/10.1016/S0040-4039(98)00594-2
  10. Jenner, G. Tetrahedron Lett. 1999, 40, 491 https://doi.org/10.1016/S0040-4039(98)02419-8
  11. Curini, M.; Epifan, F.; Marcotullio, M. C.; Rosati, O.; Rossi, M. Synlett 1999, 315
  12. Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Roncohi, A. Tetrahedron Lett. 2001, 42, 3041 https://doi.org/10.1016/S0040-4039(01)00368-9
  13. Bandini, M.; Cozzi, P. G.; Garelli, A.; Melchiorre, P.; Umani-Ronchi, A. Eur. J. Org. Chem. 2002, 3243
  14. Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Synlett 2002, 793
  15. Chen, F.; Feng, X.; Qin, B.; Zhang, G.; Jiang, Y. Synlett 2003, 558
  16. Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Tetrahedron 2003, 59, 5667 https://doi.org/10.1016/S0040-4020(03)00908-6
  17. Kim, S. S.; Song, D. H. J. Orgnomet. Chem. 2004, in press
  18. Kim, S. S.; Rajagopal, G.; Song, D. H. J. Orgnomet. Chem. 2004, 689, 1734 https://doi.org/10.1016/j.jorganchem.2004.01.025
  19. Kim, S. S.; Rajagopal, G.; Kim, D. W.; Song, D. H. Synthetic Commun. 2004, 34(16), 2973 https://doi.org/10.1081/SCC-200026652
  20. Kim, S. S.; Song, D. H. Letter. Org. Chem. 2004, 1, 264 https://doi.org/10.2174/1570178043400884
  21. Evans, D. A.; Truesdale, L. K. Tetrahedron Lett. 1973, 49, 4929
  22. Takashi, O.; Tomoya, M.; Keisuke, T.; Hayato, I.; Keiji, M. Tetrahedron 2001, 57, 867 https://doi.org/10.1016/S0040-4020(00)01040-1

Cited by

  1. Mild and Efficient Silylcyanation of Aldehydes Catalyzed by Zirconium Complex. vol.36, pp.25, 2005, https://doi.org/10.1002/chin.200525033
  2. Enantioselective cyanosilylation of aldehydes catalyzed by Mn(salen) complex/triphenyl phosphine oxide vol.21, pp.9, 2007, https://doi.org/10.1002/aoc.1284