Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Phosphomolybdic Acid Supported on Silica Gel as an Efficient and Reusable Catalyst for Cyanosilylation of Aldehydes

  • Published : 2008.07.20
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Abstract

Phosphomolybdic acid supported on silica gel (PMA-$SiO_2$) is an efficient catalyst for the activation of TMSCN for the facile cyanosilylation of various aldehydes. Cyano transfer from TMSCN to aldehyde proceeds smoothly at rt in presence of 0.8 mol % of PMA-$SiO_2$ leading to a range of cyanosilylether in excellent yield (mostly over 93%) within short reaction time (30 min). The catalyst can be recovered and reused several times without loss of activity.

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References

  1. North, M. Tetrahedron: Asymmetry 2003, 14, 147 https://doi.org/10.1016/S0957-4166(02)00825-X
  2. Brunel, J. M.; Holmes, P. I. Angew. Chem. Int. Ed. 2004, 43, 2752 https://doi.org/10.1002/anie.200300604
  3. Gregory, R. J. H. Chem. Rev. 1999, 99, 3649 https://doi.org/10.1021/cr9902906
  4. Furin, G. G.; Vyazankina, O. A.; Gostevasky, B. A.; Vyazankin, N. S. Tetrahedron 1988, 44, 2675
  5. Rasmussen, J. K.; Heilmann, S. M.; Krepski, L. R.; Larson, G. L. Ed. JAI Press London 1991, 1, 65
  6. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106 https://doi.org/10.1021/ja0475959
  7. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384 https://doi.org/10.1021/ja050543e
  8. Jacobsen, E. N.; Fuerst, D. E. J. Am. Chem. Soc. 2005, 127, 8964 https://doi.org/10.1021/ja052511x
  9. Hamsshima, Y. S. D.; Shibasaki, K. M. J. Am. Chem. Soc. 1999, 121, 2641 https://doi.org/10.1021/ja983895c
  10. Fetterly, B. M.; Verkade, J. H. Tetrahedron Lett. 2005, 46, 8061 https://doi.org/10.1016/j.tetlet.2005.09.032
  11. Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515 https://doi.org/10.1021/jo00058a037
  12. Hatano, M.; Lkeno, T.; Miyamoto, T.; Ishihara, K. J. Am. Chem. Soc. 2005, 127, 10776 https://doi.org/10.1021/ja051125c
  13. Karimi, B.; Ma'man, L. Org. Lett. 2004, 4813
  14. Song, J. J.; Gallou, J. T.; Reeves, J. T.; Tan, Z.; Yee, N. K.; Senanake, C. H. J. Org. Chem. 2006, 71, 1273 https://doi.org/10.1021/jo052206u
  15. Wang, L.; Huang, X.; Jiang, J.; Liu, X.; Feng, X. Tetrahedron Lett. 2006, 47, 1581 https://doi.org/10.1016/j.tetlet.2005.12.135
  16. Kim, S. S.; Rajagopal, G.; Song, D. G. J. Organomet. Chem. 2004, 689, 1734 https://doi.org/10.1016/j.jorganchem.2004.01.025
  17. Kim, S. S.; Rajagopal, G. Synthesis 2007, 2, 215
  18. Kim, S. S.; Lee, S. H.; Kwak, J. M. Tetrahedron: Asymmetry 2006, 17, 1165 https://doi.org/10.1016/j.tetasy.2006.04.011
  19. Kim, S. S.; Song, D. H. Eur. J. Org. Chem. 2005, 1777
  20. Kim, S. S.; Lee, S. H. Synthetic Comun. 2005, 35, 751 https://doi.org/10.1081/SCC-200050390
  21. Kim, S. S.; Kim, D. W.; Rajgopal, G. Synthesis 2004, 2, 213
  22. Kim, S. S.; Song, D. H. Lett. Org. Chem. 2004, 1, 264 https://doi.org/10.2174/1570178043400884
  23. Kim, S. S. Pure and Applied Chem. 2006, 78, 977 https://doi.org/10.1351/pac200678050977
  24. Kim, S. S.; George, S. C. Bull. Korean Chem. Soc. 2007, 28, 1167 https://doi.org/10.5012/bkcs.2007.28.7.1167
  25. Kim, S. S.; Kwak, J. M. Tetrahedron 2006, 62, 49 https://doi.org/10.1016/j.tet.2005.09.131
  26. Kim, S. S.; George, S. C.; Kadam, S. T. Appl. Organometallic Chem. 2007, 21, 994 https://doi.org/10.1002/aoc.1324
  27. Kim, S. S.; Kwak, J. M.; George, S. C. Appl. Organometallic Chem. 2007, 21, 809 https://doi.org/10.1002/aoc.1284
  28. Kozhevnikov, I. V. Russ. Chem. Rev. 1987, 56, 811 https://doi.org/10.1070/RC1987v056n09ABEH003304
  29. Firouzabadi, H.; Iranpoor, N.; Amani, K. Synthesis 2003, 408
  30. Kozhevnikova, E. F.; Derouane, E. G.; Kozhevniko, I. V. Chem. Commun. 2002, 1178
  31. Kishore Kumar, G. D.; Baskaran, S. Synlett 2004, 1719
  32. Yadav, J. S.; Raghavendra, S.; Satyanarayana, M.; Balanarasaiah, E. Synlett 2005, 2461
  33. Kishore Kumar, G. D.; Baskaran, S. J. Org. Chem. 2005, 70, 4520 https://doi.org/10.1021/jo0502697
  34. Kim, S. S.; Kadam, S. T. Synthesis 2008, 2, 267
  35. Shen, Z. L.; Ji, S. J.; Loh, T. P. Tetrahedron Lett. 2005, 46, 3137 https://doi.org/10.1016/j.tetlet.2005.01.177
  36. Lakshimikantm, M.; Seekanth, P.; Santhi, P. L. Green Chem. 2000, 47
  37. Suzuki, Y.; Abu Bakar, M. D.; Sato, M. Tetrahedron 2005, 62, 4227 https://doi.org/10.1016/j.tet.2006.01.101
  38. Khan, N-UL.; Agrawal, R. K.; Abdi, S. H. R.; Sing, S.; Jasra, R. V. J. Organomet. Chem. 2007, 692, 4361 https://doi.org/10.1016/j.jorganchem.2007.07.011
  39. Mei, L. J. Mol. Catal. A 2005, 227, 183 https://doi.org/10.1016/j.molcata.2004.10.028
  40. Fetterly, B. M.; Verkade, J. G. Tetrahedron Lett. 2005, 46, 8061 https://doi.org/10.1016/j.tetlet.2005.09.032
  41. De, S. K.; Gibbs, R. A. J. Mol. Catal A 2005, 232, 123 https://doi.org/10.1016/j.molcata.2005.01.034
  42. Saravanan, P.; Anand, R. V.; Singh, V. K. Tetrahedron Lett. 1998, 39, 3823 https://doi.org/10.1016/S0040-4039(98)00594-2
  43. Kurono, N.; Yamaguchi, M.; Suzuki, K.; Ohkuma, T. J. Org. Chem. 2005, 70, 6530 https://doi.org/10.1021/jo050791t
  44. Zhang, G.; He, T.; Chen, Y.; Yang, W.; Yao, J. Phys. Chem. Phys. 2003, 5, 2751 https://doi.org/10.1039/b305377f
  45. Amini, M. M.; Shaabani, A.; Bazgir, A. Cata. Commun. 2006, 7, 843 https://doi.org/10.1016/j.catcom.2006.02.027

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