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Chemoselective Iodination of Alcohols with CeCl3·7H2O/NaI over SiO2 under Microwave Irradiation

  • Published : 2004.08.20

Abstract

A simple and effective procedure for conversion of primary, secondary, allylic and benzylic alcohols into the corresponding iodides is described using $CeCl_3{\cdot}7H_2O/NaI\;over\;SiO_2$ under microwave irradiation. Benzylic alcohols are selectively converted in the presence of saturated alcohols into their corresponding benzylic iodides under these conditions.

Keywords

References

  1. Posner, G. H. Angew. Chem. Int. Ed. Engl. 1978, 17, 487. https://doi.org/10.1002/anie.197804871
  2. Mckillop, A.; Young, D. W. Synthesis 1979, 401.
  3. Cornelis, A.; Laszlo, P. Synthesis 1985, 909.
  4. Laszlo, P.Preparative Chemistry Using Supported Reagents; AcademicPress, Inc: San Diego, 1987.
  5. Smith, K. Solid Supports andCatalyst in Organic Synthesis; Ellis Horwood: Chichester, 1992.
  6. Balogh, M.; Laszlo, P. Organic Chemistry Using Clays;Springer: Berlin, 1993.
  7. Clark, J. H. Catalysis of OrganicReactions by Supported Inorganic Reagents; VCH: NY, 1994.
  8. Clark, J. H.; Macquarri, D. J. Chem. Commun. 1998, 853.
  9. Kabalka, G. W.; Pagni, R. M.; Tetrahedron 1997, 53, 7999. https://doi.org/10.1016/S0040-4020(97)00264-0
  10. Caddick, S. Tetrahedron 1995, 51, 10403. https://doi.org/10.1016/0040-4020(95)00662-R
  11. Cornelis, A.;Laszlo, P. Synlett 1994, 155.
  12. Touaux, B.; Klein, B.; Boullet, F.; Hamelin, J. J. Chem. Res (S)1994, 116.
  13. Clark, J. H.; Kybett, A. P.; Macquarrie, D. J.;Barlow, S. J.; London, P. J. Chem. Soc. Chem. Commun. 1989,1353.
  14. Laszlo, P.; Lucchetti, J. Tetrahedron Lett. 1984, 25,1567. https://doi.org/10.1016/S0040-4039(01)90012-7
  15. Varma, R. S. Green Chem. 1999, 1, 43. https://doi.org/10.1039/a808223e
  16. Loupy, A.; Petit, J.;Hamelin, F.; Texier Boullet, Jacquault, Mathe, D. Synthesis 1998,1213.
  17. Bohlmann, R. In Comprehensive Organic Synthesis; Trost,B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp203-223.
  18. Hudlicky, M.; Hudlicky, T. In The Chemistry ofFunctional Groups; Supplement, D.; Patai, S.; Rappoport, Z.,Eds.; Wiley: New York, 1983; p 1021.
  19. Chambers, R. D.; James, S. R. In Comprehensive Organic Chemistry; Barton, D.; Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, pp 493- 575.
  20. Su, M. D.; Chu, S. Y. J. Am. Chem. Soc. 1999, 121, 1045. https://doi.org/10.1021/ja9831148
  21. Wakefield, B. J. In Organolithium Methods; Academic Press:London, 1988.
  22. Marsden, S. P. Contemp. Org. Synth. 1997, 4, 118, and referencestherein. https://doi.org/10.1039/co9970400118
  23. Villieras, J.; Bacquet, C.; Normant, J. F. Bull. Chem. Soc. Fr. 1975,1797.
  24. Landauer, S. R.; Rydon, H. N. J. Chem. Soc. 1953, 2224. https://doi.org/10.1039/jr9530002224
  25. Coe, D. G.; Landauer, S. R.; Rydon, H. N. J. Chem. Soc. 1954,2281. https://doi.org/10.1039/jr9540002281
  26. Rydon, H. N.; Tonge, B. L. J. Chem. Soc. 1956, 3043. https://doi.org/10.1039/jr9560003043
  27. Crofts, P. C.; Downie, I. M. J. Chem. Soc. 1963, 2559.
  28. Lee,J. B.; Nolan, T. J. Can. J. Chem. 1966, 44, 1331. https://doi.org/10.1139/v66-199
  29. Havlock, C.R.; Melton, L. D.; Slessor, K. N.; Tracey, A. S. Carbohydr. Res.1971, 16, 375. https://doi.org/10.1016/S0008-6215(00)81173-8
  30. Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem.1972, 37, 2289. https://doi.org/10.1021/jo00979a018
  31. Hanessian, S.; Ponpipom, M. M.; Lavallee, P.Carbohydr. Res. 1972, 24, 45. https://doi.org/10.1016/S0008-6215(00)82258-2
  32. Garegg, P. J.; Samuelsson, B. J.Chem. Soc. Perkin Trans. 1 1980, 2866. https://doi.org/10.1039/p19800002866
  33. Garegg, P. J.;Johansson, R.; Ortega, C.; Samuelsson, B. J. Chem. Soc. PerkinTrans 1 1982, 681. https://doi.org/10.1039/p19820000681
  34. Joseph, R.; Pallan, P. S.; Sudalai, A.;Ravindranathan, T. Tetrahedron Lett. 1995, 36, 609. https://doi.org/10.1016/0040-4039(94)02315-3
  35. Jung, M. E.; Ornstein, P. L. Tetrahedron Lett. 1977, 2659.
  36. Jung, M. E.; Hatfield, G. L. Tetrahedron Lett. 1978, 4483.
  37. Morita, T.; Yoshida, S.; Okamoto, Y.; Sakurai, H. Synthesis 1979,379.
  38. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R.J. Org. Chem. 1979, 44, 1247. https://doi.org/10.1021/jo01322a012
  39. Olah, G. A.; Narang, S. C.;Gupta, B. G. B.; Malhotra, R. Angew. Chem. Int. Ed. Engl. 1979,18, 612. https://doi.org/10.1002/anie.197906121
  40. Lauwers, M.; Regnier, B.; Van Eenoo, M.; Denis, J.N.; Krief, A. Tetrahedron Lett. 1979, 1801.
  41. Reddy, Ch. K.;Periasamy, M. Tetrahedron Lett. 1989, 30, 5663. https://doi.org/10.1016/S0040-4039(01)93826-2
  42. Deo, M. D.;Marcantoni, E.; Torregiani, E.; Bartoli, G.; Bellucci, M. C.; Bosco,M.; Sambri, L. J. Org. Chem. 2000, 65, 2830. https://doi.org/10.1021/jo991894c
  43. Kad, G. L.; Kaur,J.; Bansal, P.; Singh, J. J. Chem. Research(S) 1996, 188.
  44. Bandgar, B. P.; Sadavarte, V. S.; Bettigeri, S. V. Monatsh. Chem.2002, 133, 345. https://doi.org/10.1007/s007060200013
  45. Olah, G. A.; Hussain, Singh, A. B. P.; Mehrotra, A. K. J. Org.Chem. 1983, 48, 3667. https://doi.org/10.1021/jo00169a010
  46. Mandal, A. K.; Mahajan, S. W.Tetrahedron Lett. 1985, 26, 3863. https://doi.org/10.1016/S0040-4039(00)89271-0
  47. Vankar, Y. D.; Rao, C. T.Tetrahedron Lett. 1985, 26, 2717. https://doi.org/10.1016/S0040-4039(00)98145-0
  48. Classon, B.; Liu, Z.;Samuelsson, B. J. Org. Chem. 1988, 53, 6126. https://doi.org/10.1021/jo00261a032
  49. Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S. K.; Sabitha, G.Synlett 2001, 1134.
  50. Ballini, R.; Marcantoni, E.; Perrella, S. J.Org. Chem. 1999, 64, 2954. https://doi.org/10.1021/jo982131c
  51. Alessandrini, S.; Bartoli, G.;Belluci, M. C.; Dalpozzo, R.; Malavolta, M.; Marcantoni, E.;Sambri, L. J. Org. Chem. 1999, 64, 1986. https://doi.org/10.1021/jo9821574
  52. Imamoto, T. Lanthanides in Organic Synthesis; Academic Press:New York, 1994.
  53. Ponde, D.; Borade, H. B.; Sudalai, A.; Ravindranathan, T.;Deshpande, V. H. Tetrahedron Lett. 1996, 37, 4605 and referencescited therein https://doi.org/10.1016/0040-4039(96)00888-X
  54. Vogel, A. Vogel's A Text Book of Practical Organic Chemistry,4th ed; Longman, 1978.
  55. Dictionary of Organic Compound, 6thed; Chapman and Hall: London, 1995.

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