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Research on Chemical Intermediates

, Volume 19, Issue 8, pp 755–775 | Cite as

Progress of the Barton-McComble Methodology: From tin hydrides to Silanes

  • C. Chatgilialoglu
  • C. Ferreri
Article

Abstract

Use of organosilanes that promote the Barton-McCombie deoxygenation is an emerging methodology for organic transformations. A comparison between a variety of substituted silanes is presented. (Me3Si)3SiH rivals Bu3SnH in efficiency and it is a superior reagent from ecological and practical perspectives.

Keywords

Xanthate Radical Chain Reaction Deuteride Thiocarbonyl Methyl Elaidate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References and notes

  1. 1.
    For example, see: a) B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986; b) D.P. Curran, Synthesis 417 (1988) and 489 (1988); c) C.P. Jasperse, D.P. Curran, and T.L. Fevig, Chem. Rev. 91, 1237 (1991); d) D.P. Curran in B.M. Trost and I. Fleming (Eds.), Comprehensive Organic Synthesis, Vol. 4, Pergamon Press, Oxford, 1992, Chapters 1 and 2; e) W.B. Motherwell and D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992.Google Scholar
  2. 2.
    D.H.R. Barton and S.W. McCombie, J. Chem. Soc., Perkin Trans. 1 1574 (1975).Google Scholar
  3. 3.
    D.H.R. Barton and W.B. Motherwell, Pure and Appl. Chem. 53 15 (1981).CrossRefGoogle Scholar
  4. 4.
    W. Hartwig, Tetrahedron 39 2609 (1983).CrossRefGoogle Scholar
  5. 5.
    M. Pereyre, J.-P. Quintard, and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987, pp. 84–97.Google Scholar
  6. 6.
    W.P. Neumann, Synthesis 665 (1987).Google Scholar
  7. 7.
    D.M. Huryn and M. Okabe, Chem. Rev. 92 1745 (1992).CrossRefGoogle Scholar
  8. 8.
    a) M.J. Robins and J.S. Wilson, J. Am. Chem. Soc. 103, 933 (1981); b) M.J. Robins, J.S. Wilson, and F. Hansske, J. Am. Chem. Soc. 105, 4059 (1983).CrossRefGoogle Scholar
  9. 9.
    a) D.H.R. Barton and J. Cs. Jaszberenyi, Tetrahedron Lett. 30 2619 (1989); b) D.H.R. Barton, J. Dorchak, and J. Cs. Jaszberenyi, Tetrahedron 48, 7435 (1992).CrossRefGoogle Scholar
  10. 10.
    a) D.H.R. Barton, W.B. Motherwell, and A. Stange, Synthesis 743 (1981); b) D.H.R. Barton, P. Blundell, J. Dorchak, D.O. Jang, and J. Cs. Jaszberenyi, Tetrahedron 47 8969 (1991).Google Scholar
  11. 11.
    a) D.H.R. Barton and R. Subramanian, J. Chem. Soc., Chem. Commun. 867 (1976); b) D.H.R. Barton and R. Subramanian, J. Chem. Soc., Perkin Trans. 1 1718 (1977); c) H. Redlich, W. Sudan, and H. Paulsen, Tetrahedron 41, 4253 (1985).Google Scholar
  12. 12.
    D.H.R. Barton, W. Hartwig, R.S. Hay-Motherwell, W.B. Motherwell, and A. Stange, Tetrahedron Lett. 23 2019 (1982).CrossRefGoogle Scholar
  13. 13.
    D.H.R. Barton, S.I. Parekh, and C.-L. Tse, Tetrahedron Lett. 34, 2733 (1993).CrossRefGoogle Scholar
  14. 14.
    a) A.G.M. Barrett, D.H.R. Barton, R. Bielski, and S.W. McCombie, J. Chem. Soc., Chem. Commun. 8 (1977); b) A.G.M. Barrett, D.H.R. Barton, and R. Bielski, J. Chem. Soc., Perkin Trans. 1 2378 (1979); c) D.H.R. Barton, D.K. Zheng, and S.D. Gero, J. Carbohyd. Chem. 1 105 (1982); d) B. Lythgoe and I. Waterhouse, Tetrahedron Lett. 4223 (1977); e) D.H.R. Barton, R.S. Hay-Motherwell, and W.B. Motherwell, J. Chem. Soc., Perkin Trans 1 2363 (1981).Google Scholar
  15. 15.
    a) J.J. Patroni and R.V. Stick, J. Chem. Soc., Chem. Commun. 449 (1978); b) J.J. Patroni and R.V. Stick, Aust. J. Chem. 32 411 (1979).Google Scholar
  16. 16.
    For example, see: F. Minisci in C. Chatgilialoglu and K.-D. Asmus (Eds.), Sulfur-Centered Reactive Intermediates in Chemistry and Biology, Plenum Press, New York, 1990, pp. 303–317.Google Scholar
  17. 17.
    P.J. Barker and A.L.J. Beckwith, J. Chem. Soc.. Chem. Commun. 683 (1984).Google Scholar
  18. 18.
    D.H.R. Barton, D. Crich, A. Lobberding, and S.Z. Zard, Tetrahedron 42, 2329 (1986).CrossRefGoogle Scholar
  19. 19.
    M.D. Bachi and E. Bosch, J. Chem. Soc. Perkin Trans. 1 1517 (1988).Google Scholar
  20. 20.
    D.H.R. Barton, D.O. Jang, and J. Cs. Jaszberenyi, Tetrahedron Lett. 31, 3991 (1990).CrossRefGoogle Scholar
  21. 21.
    K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett. 29, 6125 (1988).CrossRefGoogle Scholar
  22. 22.
    a) M. Gerlach, F. Jordens, H. Kuhn, W.P. Neumann, and M. Peterseim, J. Org. Chem. 56, 5971 (1991); b) W.P. Neumann and M. Peterseim, Synlett 801 (1992).CrossRefGoogle Scholar
  23. 23.
    E. Vedejs, S.M. Duncan, and A.R. Haight, J. Org. Chem. 58 3046 (1993).CrossRefGoogle Scholar
  24. 24.
    J. Boivin, J. Camara, and S. Z. Zard, J. Am. Chem. Soc. 114, 7909 (1992).CrossRefGoogle Scholar
  25. 25.
    For a review, see: C. Chatgilialoglu, Acc. Chem. Res. 25 188 (1992).CrossRefGoogle Scholar
  26. 26.
    Reagent of the year 1990 (Fluka award).Google Scholar
  27. 27.
    M. Ballestri, C. Chatgilialoglu, K.B. Clark, D. Griller, B. Giese, and B. Kopping, J. Org. Chem. 56, 678 (1991).CrossRefGoogle Scholar
  28. 28.
    C. Chatgilialoglu, J. Dickhaut, and B. Giese, J. Org. Chem. 56, 6399 (1991).CrossRefGoogle Scholar
  29. 29.
    D. Schummer and G. Höfle, Synlett 705 (1990).Google Scholar
  30. 30.
    D.H.R. Barton, D.O. Jang, and J. Cs. Jaszberenyi, Tetrahedron Lett. 32, 4684 (1990).Google Scholar
  31. 31.
    K. Weinges, H. Schick, and P. Zollner, Liebigs Ann. Chem. 293 (1992).Google Scholar
  32. 32.
    C. Ferreri, M. Ballestri, G. Barbaro, A. Battaglia, and C. Chatgilialoglu, manuscript in preparation.Google Scholar
  33. 33.
    C. Chatgilialoglu, A. Guerrini, and M. Lucarini, J. Org. Chem. 57, 3405 (1992).CrossRefGoogle Scholar
  34. 34.
    M. Ballestri, C. Chatgilialoglu, M. Guerra, A. Guerrini, M. Lucarini, and G. Seconi, J. Chem. Soc. Perkin Trans 2 421 (1993).Google Scholar
  35. 35.
    a) C. Chatgilialoglu, A. Guerrini, and G. Seconi, Synlett 219 (1990); b) C. Chatgilialoglu, M. Guerra, A. Guerrini, G. Seconi, K.B. Clark, D. Griller, J. Kanabus-Kamiska, and J.A. Martinho- Simões, J. Org. Chem. 57 2427 (1992).Google Scholar
  36. 36.
    a) J.N. Kirwan, B.P. Roberts, and C.R. Willis, Tetrahedron Lett. 31, 5093 (1990); b) S.J. Cole, J.N. Kirwan, B.P. Roberts, and C.R. Willis, J. Chem.Soc., Perkin Trans. 1 103 (1991).CrossRefGoogle Scholar
  37. 37.
    For a review, see: D.H.R. Barton, Tetrahedron 48, 2529 (1992).CrossRefGoogle Scholar
  38. 38.
    D.H.R. Barton, D.O. Jang, and J. Cs. Jaszberenyi, Synlett 435 (1991).Google Scholar
  39. 39.
    D.H.R. Barton, D.O. Jang, and J. Cs. Jaszberenyi, Tetrahedron 49 2793 (1993).CrossRefGoogle Scholar
  40. 40.
    D.H.R. Barton, D.O. Jang, and J. Cs. Jaszberenyi, Tetrahedron Lett. 32, 2569 (1991).CrossRefGoogle Scholar
  41. 41.
    a) D.H.R. Barton, J. Cs. Jaszberenyi, and C. Tachdjian, Tetrahedron Lett. 32 2703 (1991); b) D.H.R. Barton and C. Tachdjian, Tetrahedron 32 7109 (1992).CrossRefGoogle Scholar
  42. 42.
    D.H.R. Barton, D.O. Jang, J. Cs. Jaszberenyi, Tetrahedron Lett. 32, 7187 (1991).CrossRefGoogle Scholar
  43. 43.
    a) J. Lusztyk, J. Maillard, and K.U. Ingold, J. Org. Chem. 51 2457 (1986); b) M. Newcomb and S.U. Park, J. Am. Chem. Soc. 108, 4132 (1986).CrossRefGoogle Scholar
  44. 44.
    Treatment of R’C(O)OR with Ph3SiH in the presence of t-BuOOBu-t (1 equiv) at 140 00B0;C gave the RH in good yield [H. Sano, M. Ogata, and T. Migita, Chem. Lett. 77 (1986)].Google Scholar
  45. 45.
    Primary and secondary chloroformates reduced to the corresponding alkanes in a sealed tube using n-Pr3SiH and t-BuOOBu-t (ca. I equiv) at 140 °C [R.A. Jackson and F. Malek, J. Chem. Soc, Perkin Trans. 1, 1207 (1980)].Google Scholar
  46. 46.
    C. Chatgilialoglu, C. Ferreri, and M. Lucarini, J. Org. Chem. 58 249 (1993).CrossRefGoogle Scholar
  47. 47.
    F. Coppa, F. Fontana, F. Minisci, G. Pianese, P. Tortoreto, and L. Zhao, Tetrahedron Lett. 33, 687 (1992).CrossRefGoogle Scholar
  48. 48.
    C. Chatgilialoglu, K.U. Ingold, J. Lusztyk, A.S. Nazran, and J.C. Scaiano, Organometallics 2, 1332 (1983).CrossRefGoogle Scholar
  49. 49.
    See, for example: D.H.R. Barton Aldrichimica Acta 23, 3 (1990).Google Scholar
  50. 50.
    B. Giese, J.A. Gonzales-Gomez, and T. Witzel, Angew. Chem. Int. Ed. Engl. 23 96 (1984).CrossRefGoogle Scholar
  51. 51.
    P. Bouquet, C. Loustau Cazalet, Y. Chapleur, S. Samreth, and F. Bellamy, Tetrahderon Lett. 33 1997 (1992).CrossRefGoogle Scholar
  52. 52.
    D.H.R. Barton, D.O. Jang, and J. Cs. Jaszberenyi, Tetrahedron Lett. 33, 6629 (1992).CrossRefGoogle Scholar
  53. 53.
    The first observation of this effect has been studied by Robert Rosenthal, see: a) R. Rosenthal and L. Jacobson, Pygamalion in the Classroom: Teachers’ Expectations and Pupils’ Intellectual Development, Holt, Rinehart and Winston, New York, 1968; b) R. Rosenthal in R. Luccio (Ed.), Soggetti e Sperimentatori nella Ricerca Psicologica, Mulino, Bologna, 1982, pp. 75-149.Google Scholar
  54. 54.
    D.W. Johnson and A. Poulos, Tetrahedron Lett. 33, 2045 (1992).CrossRefGoogle Scholar
  55. 55.
    C. Ferreri, M. Ballestri, and C. Chatgilialoglu, Tetrahedron Lett. 34 5147 (1993).CrossRefGoogle Scholar
  56. 56.
    G. Emmer and S. Weber-Roth, Tetrahedron 48, 5861 (1992).CrossRefGoogle Scholar
  57. 57.
    See, also: T.B. Lowinger and L. Weiler, J. Org. Chem. 57 6099 (1992).CrossRefGoogle Scholar
  58. 58.
    Note added in proofi We thank Professor D.H.R. Barton for kindly sending us a copy of his recent book (D.H.R. Barton and S.I. Parekh, Half a Century of Free Radical Chemistry, Cambridge University Press, 1993), in which he describes some of his inventions of radical reactions. In this book, chapter 4 is dedicated to the topic of deoxygenation reaction and we found the anecdote reported on the discovery of this reaction amusing. In chapter 6 S.I. Parekh reported some recent examples of the applications of the Barton-McCombie methodology.Google Scholar

Copyright information

© Springer 1993

Authors and Affiliations

  • C. Chatgilialoglu
    • 1
  • C. Ferreri
    • 2
  1. 1.I.Co.C.E.A.Consiglio Nazionale delle RicerceBolognaItaly
  2. 2.Dipartimento di Chimica Organica e BiologicaUniversitd di NapoliNapoliItaly

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