Hydrosilylation of Carbon—Carbon Multiple Bonds in Organic Synthesis

  • Bogdan Marciniec
Part of the Advances In Silicon Science book series (ADSS, volume 1)

Abstract

Growing interest in the development of sequential processes, including regio- and stereoselective hydrosilylation of functionalised alkenes and alkynes as the key step, stems from the ability to assemble stereodefined complex molecules from simple starting materials through organosilicon intermediates in a convergent and flexible manner. This chapter describes some recent advances in the sequential synthetic strategies including both transition-metal catalysed intra- and intermolecular hydrosilylation of C═C and C≡C bonds followed by desilylative oxidation, cross-coupling, proto- and halodesilylation, cycloaddition, nucleophilic addition and other transformations, leading to stereodefined organic derivatives which are widely applied as fine chemicals, synthetic building blocks or are key intermediates in total synthesis of natural products.

Keywords

Ketone Palladium Epoxidation Diene Rhodium 

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References

  1. 1.
    M.A. Brook, Silicon in Organic, Organometallic and Polymer Chemistry, Wiley, New York, 2000.Google Scholar
  2. 2.
    B.M. Trost, Z.T. Ball, Synthesis, 2005, 853–887.Google Scholar
  3. 3.
    I. Fleming, A. Barbero, D. Walter, Chem. Rev., 1997, 2063–2192.Google Scholar
  4. 4.
    G. Varchi, I. Ojima, Curr. Org. Chem., 2006, 10, 1341–1362.CrossRefGoogle Scholar
  5. 5.
    M. Bols, T. Skrydstrup, Chem. Rev., 1995, 95, 1253–1277.CrossRefGoogle Scholar
  6. 6.
    D.R. Gauthier, K.S. Zandi, K.J. Shea, Tetrahedron, 1998, 54, 2289–2338.CrossRefGoogle Scholar
  7. 7.
    G.R. Jones, Y. Landais, Tetrahedron, 1996, 52, 7599–7662.CrossRefGoogle Scholar
  8. 8.
    K. Tamao, N. Ishida, T. Tanaka, M. Kumada, Organometallics, 1983, 2, 1694–1696.CrossRefGoogle Scholar
  9. 9.
    I. Flemming, R. Henning, H. Plaut, J. Chem. Soc. Chem. Commun., 1984, 29–31.Google Scholar
  10. 10.
    G.A. Molander, Ch.P. Corrette, Organometallics, 1998, 17, 5504–5512.CrossRefGoogle Scholar
  11. 11.
    J. Yoshida, K. Itami, K. Mitsudo, S. Suga, Tetrahedron Lett., 1999, 40, 3403–3406.CrossRefGoogle Scholar
  12. 12.
    K. Tamao, T. Tanaka, T. Nakajima, R. Sumiya, H. Arai, Y. Ito, Tetrahedron Lett., 1986, 27, 3377–3380.CrossRefGoogle Scholar
  13. 13.
    K. Tamao, T. Yamauchi, Y. Ito, Chem. Lett., 1987, 171–174.Google Scholar
  14. 14.
    K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi, Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090–6093.CrossRefGoogle Scholar
  15. 15.
    Z.H. Peng, K.A. Woerpel, J. Am. Chem. Soc., 2003, 125, 6018–6019.CrossRefGoogle Scholar
  16. 16.
    K. Tamao, Y. Nakagawa, H. Arai, N. Higuchi, Y. Ito, J. Am. Chem. Soc., 1988, 110, 3712–3714.CrossRefGoogle Scholar
  17. 17.
    N.R. Curtis, A.B. Holmes, Tetrahedron Lett., 1992, 33, 675–678.CrossRefGoogle Scholar
  18. 18.
    S.Y.F. Mak, N.R. Curtis, A.N. Payne, M.S. Congreve, C.L. Francis, J.W. Burton, A.B. Holmes, Synthesis, 2005, 3199–3201.Google Scholar
  19. 19.
    S.Y.F. Mak, N.R. Curtis, A.N. Payne, M.S. Congreve, A.J. Wildsmith, C.L. Francis, J.E. Davies, S.J. Pascu, J.W. Burton, A.B. Holmes, Chem. Eur. J., 2008, 14, 2867–2885.CrossRefGoogle Scholar
  20. 20.
    J.W. Burton, J.S. Clark, S. Derrer, T.C. Stork, J.G. Bendall, A.B. Holmes, J. Am. Chem. Soc., 1997, 119, 7483–7498.CrossRefGoogle Scholar
  21. 21.
    K. Tamao, Y. Nakagawa, Y. Ito, J. Org. Chem., 1990, 55, 3438–3439.CrossRefGoogle Scholar
  22. 22.
    K. Tamao, Y. Nakagawa, Y. Ito, Organometallics, 1993, 12, 2297–2308.CrossRefGoogle Scholar
  23. 23.
    M.P. Sibi, J.W. Christensen, Tetrahedron Lett., 1995, 36, 6213–6216.CrossRefGoogle Scholar
  24. 24.
    K. Tamao, K. Maeda, T. Tanaka, Y. Ito, Tetrahedron Lett., 1988, 29, 6955–6956.CrossRefGoogle Scholar
  25. 25.
    J.A. Marshall, M.M. Yanik, Org. Lett., 2000, 2, 2173–2175.CrossRefGoogle Scholar
  26. 26.
    J.A. Marshall, K.C. Ellis, Org. Lett., 2003, 5, 1729–1732.CrossRefGoogle Scholar
  27. 27.
    S.A. Burova, F.E. McDonald, J. Am. Chem. Soc., 2004, 126, 2495–2500.CrossRefGoogle Scholar
  28. 28.
    J.A. Marshall, M.M. Yanik, J. Org. Chem., 2001, 66, 1373–1379.CrossRefGoogle Scholar
  29. 29.
    B.M. Trost, Z.T. Ball, J. Am. Chem. Soc., 2001, 123, 12726–12727.CrossRefGoogle Scholar
  30. 30.
    B.M. Trost, Z.T. Ball, J. Am. Chem. Soc., 2003, 125, 30–31.CrossRefGoogle Scholar
  31. 31.
    B.M. Trost, Z.T. Ball, J. Am. Chem. Soc., 2005, 127, 17644–17655.CrossRefGoogle Scholar
  32. 32.
    B.M. Trost, Z.T. Ball, T. Jörge, Angew. Chem. Int. Ed., 2003, 42, 3415–3418.CrossRefGoogle Scholar
  33. 33.
    B.M. Trost, Z.T. Ball, K.M. Laemmerhold, J. Am. Chem. Soc., 2005, 127, 10028–10038.CrossRefGoogle Scholar
  34. 34.
    E. Casas-Arce, B. ter Horst, B.L. Feringa, A.J. Minnaard, Chem. Eur. J., 2008, 14, 4157–4159.CrossRefGoogle Scholar
  35. 35.
    B.M. Trost, Z.T. Ball, J. Am. Chem. Soc., 2004, 126, 13942–13944.CrossRefGoogle Scholar
  36. 36.
    G.A. Molander, P.J. Nichols, J. Am. Chem. Soc., 1995, 117, 4415–4416.CrossRefGoogle Scholar
  37. 37.
    G.A. Molander, P.J. Nichols, J. Org. Chem., 1996, 61, 6040–6043.CrossRefGoogle Scholar
  38. 38.
    G.A. Molander, M.H. Schmidt, J. Org. Chem., 2000, 65, 3767–3770.CrossRefGoogle Scholar
  39. 39.
    A.R. Muci, J.E. Bercaw, Tetrahedron Lett., 2000, 41, 7609–7612.CrossRefGoogle Scholar
  40. 40.
    R.A. Widenhoefer, Acc. Chem. Res., 2002, 35, 905–913.CrossRefGoogle Scholar
  41. 41.
    T. Pei, R.A. Widenhoefer, Org. Lett., 2000, 2, 1469–1471.CrossRefGoogle Scholar
  42. 42.
    T. Pei, R.A. Widenhoefer, J. Org. Chem., 2001, 66, 7639–7645.CrossRefGoogle Scholar
  43. 43.
    T. Pei, R.A. Widenhoefer, Tetrahedron Lett., 2000, 41, 7597–7600.CrossRefGoogle Scholar
  44. 44.
    T. Shibata, S. Kadowaki, K. Takagi, Organometallics, 2004, 23, 4116–4120.CrossRefGoogle Scholar
  45. 45.
    B.M. Trost, Z.T. Ball, T. Jörge, J. Am. Chem. Soc., 2002, 124, 7922–7923.CrossRefGoogle Scholar
  46. 46.
    A. Fürstner, K. Radkowski, Chem. Commun., 2002, 2182–2183.Google Scholar
  47. 47.
    F. Lacombe, K. Radkowski, G. Seidel, A. Fürstner, Tetrahedron, 2004, 60, 7315–7324.CrossRefGoogle Scholar
  48. 48.
    A. Fürstner, M. Bonnekessel, J.T. Blank, K. Radkowski, G. Seidel, F. Lacombe, B. Gabor, R. Mynott, Chem. Eur. J., 2007, 13, 8762–8783.CrossRefGoogle Scholar
  49. 49.
    B.M. Trost, M.L. Crawley, Chem. Eur. J., 2004, 10, 2237–2252.CrossRefGoogle Scholar
  50. 50.
    T. Sanada, T. Kato, M. Mitani, A. Mori, Adv. Synth. Catal., 2006, 348, 51–54.CrossRefGoogle Scholar
  51. 51.
    A. Giraud, O. Provot, A. Hamze, J.D. Brion, M. Alami, Tetrahedron Lett., 2008, 49, 1107–1110.CrossRefGoogle Scholar
  52. 52.
    J.A. Marshall, H.R. Chobanian, M.M. Yanik, Org. Lett., 2001, 3, 4107–4110.CrossRefGoogle Scholar
  53. 53.
    M.R. Hale, A.H. Hoveyda, J. Org. Chem., 1992, 57, 1643–1645.CrossRefGoogle Scholar
  54. 54.
    D.G.J. Young, M.R. Hale, A.H. Hoveyda, Tetrahedron Lett., 1996, 37, 827–830.CrossRefGoogle Scholar
  55. 55.
    S.A. Kozmin, Org. Lett., 2001, 3, 755–758.CrossRefGoogle Scholar
  56. 56.
    S.E. Denmark, D.C. Forbes, Tetrahedron Lett., 1992, 33, 5037–5040.CrossRefGoogle Scholar
  57. 57.
    X. Wang, H. Chakrapani, J.W. Madine, M.A. Keyerleber, R.A. Widenhoefer, J. Org. Chem., 2002, 67, 2778–2788.CrossRefGoogle Scholar
  58. 58.
    B.M. Fan, J.H. Xie, S. Li, L.X. Wang, Q.L. Zhou, Angew. Chem., Int. Ed., 2007, 46, 1275–1277.CrossRefGoogle Scholar
  59. 59.
    T. Hiyama, Handbook of Organopalladium Chemistry for Organic Synthesis, (E. Negishi, A. de Meijere, eds.) John Wiley & Sons: New York, 2002. vol. 1, p. 285.Google Scholar
  60. 60.
    S.E. Denmark, R.F. Swieis, Metal-Catalysed Cross-Coupling Reactions; 2nd Ed.,(F. Diederich, A. de Meijere, eds.) Wiley-VCH, Weinheim, 2004. vol. 1, Chapter 4.Google Scholar
  61. 61.
    T. Hiyama, E. Shirakawa, Top. Curr. Chem., 2002, 219, 61–85.CrossRefGoogle Scholar
  62. 62.
    J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons: Chichister, UK, 2004, pp. 338–351.Google Scholar
  63. 63.
    K. Takahashi, T. Minami, Y. Ohara, T. Hiyama, Bull. Chem. Soc. Jpn., 1995, 68, 2649–2656.CrossRefGoogle Scholar
  64. 64.
    K. Takahashi, T. Minami, Y. Ohara, T. Hiyama, Tetrahedron Lett., 1993, 34, 8263–8266.CrossRefGoogle Scholar
  65. 65.
    K. Tamao, K. Kobayashi, Y. Ito, Tetrahedron Lett., 1989, 30, 6051–6054.CrossRefGoogle Scholar
  66. 66.
    A. Mori, E. Takahisa, Y. Yamamura, T. Kato, A.P. Mudalige, H. Kajiro, K. Hirabayashi,Y. Nishihara, T. Hiyama, Organometallics, 2004, 23, 1755–1765.CrossRefGoogle Scholar
  67. 67.
    E. Alacid, C. Najera, J. Org. Chem., 2008, 73, 2315–2322.CrossRefGoogle Scholar
  68. 68.
    S.E. Denmark, Z. Wang, Org. Lett., 2001, 3, 1073–1076.CrossRefGoogle Scholar
  69. 69.
    S.E. Denmark, D. Wehrli, Org. Lett., 2000, 2, 565–568.CrossRefGoogle Scholar
  70. 70.
    Y. Nakao, J. Chen, M. Tanaka, T. Hiyama, J. Am. Chem. Soc., 2007, 129, 11694–11695.CrossRefGoogle Scholar
  71. 71.
    Y. Nakao, H. Imanaka, J. Chen, A. Yada, T.Hiyama, J. Organomet. Chem., 2007, 692, 585–603.CrossRefGoogle Scholar
  72. 72.
    C. Thiot, M. Schmutz, A. Wagner, Ch. Mioskowski, Chem. Eur. J., 2007, 13, 8971–8978.CrossRefGoogle Scholar
  73. 73.
    B.M. Trost, M.R. Machacek, Z.T. Ball, Org. Lett., 2003, 5, 1895–1898.CrossRefGoogle Scholar
  74. 74.
    S.E. Denmark, W. Pan, Org. Lett., 2001, 3, 61–64.CrossRefGoogle Scholar
  75. 75.
    S.E. Denmark, W. Pan, Org. Lett., 2002, 4, 4163–4166.CrossRefGoogle Scholar
  76. 76.
    S.E. Denmark, W. Pan, Org. Lett., 2003, 5, 1119–1122.CrossRefGoogle Scholar
  77. 77.
    L.W. Chung, Y.D. Wu, B.M. Trost, Z.T. Ball, J. Am. Chem. Soc., 2003,125, 11578–11582.CrossRefGoogle Scholar
  78. 78.
    S.V. Maifeld, D. Lee, Org. Lett., 2005, 7, 4995–4998.CrossRefGoogle Scholar
  79. 79.
    K. Tamao, K. Kobayashi, Y. Ito, J. Am. Chem. Soc., 1989, 111, 6478–6480.CrossRefGoogle Scholar
  80. 80.
    S.E. Denmark, J.H.Ch. Liu, J. Am. Chem. Soc., 2007, 129, 3737–3744.CrossRefGoogle Scholar
  81. 81.
    R.B. Miller, G. McGarvey, J. Org. Chem., 1978, 43, 4424–4431.CrossRefGoogle Scholar
  82. 82.
    M. Nagao, K. Asano, K. Umeda, H. Katayama, F. Ozawa, J. Org. Chem., 2005, 70, 10511–10514.CrossRefGoogle Scholar
  83. 83.
    H. Katayama, M. Nagao, T. Nishimura, Y. Matsui, K. Umeda, K. Akamatsu, T. Tsuruoka, H. Nawafune, F. Ozawa, J. Am. Chem. Soc. 2005, 127, 4350–4353.CrossRefGoogle Scholar
  84. 84.
    A.M. Caporusso, S. Barontini, P. Petrici, G. Vitulli, P. Salvadori, J. Organomet. Chem., 1998, 564, 57–59.CrossRefGoogle Scholar
  85. 85.
    E.O. Onyango, J. Tsurumoto, N. Imai, K. Takahashi, J. Ishihara, S. Hatakeyama, Angew. Chem. Int. Ed., 2007, 46, 6703–6705.CrossRefGoogle Scholar
  86. 86.
    S.K. Kang, Y.T. Hong, J.H. Lee, W.Y. Kim, I. Lee, Ch.M. Yu, Org. Lett., 2003, 5, 2813-2816.CrossRefGoogle Scholar
  87. 87.
    R.R. Pidaparthi, M.E. Welker, Tetrahedron Lett., 2007, 48, 7853–7856.CrossRefGoogle Scholar
  88. 88.
    C. Liu, R.A. Widenhoefer, Organometallics, 2002, 21, 5666–5673.CrossRefGoogle Scholar
  89. 89.
    I. Ojima, N. Clos, R.J. Donovan, P. Ingallina, Organometallics, 1990, 9, 3127–3133.CrossRefGoogle Scholar
  90. 90.
    S. Oi, Y. Honma, Y. Inoue, Org. Lett., 2002, 4, 667–669.CrossRefGoogle Scholar
  91. 91.
    S. Oi, A. Taira, Y. Honma, Y. Inoue, Org. Lett., 2003, 5, 97–99.CrossRefGoogle Scholar
  92. 92.
    J.W. Faller, D.G. D’Alliessi, Organometallics, 2002, 21, 1743–1746.CrossRefGoogle Scholar
  93. 93.
    Y. Otomaru, T. Hayashi, Tetrahedron Asymmetry, 2004, 15, 2647–2651.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2009

Authors and Affiliations

  • Bogdan Marciniec
    • 1
  1. 1.Faculty of ChemistryA. Mickiewicz UniversityGrunwaldzka 6Poland

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