Advertisement

Reactions Involving the Transition Metals

  • Francis A. Carey
  • Richard J. Sundberg
Part of the Advanced Organic Chemistry book series (AOC)

Abstract

While the main-group metals, especially magnesium and lithium, were the first metals to have a prominent role in organic synthesis, several of the transition metals have also become very important. In this chapter, we will discuss the reactions of transition metal compounds and intermediates that are important in the repertoire of synthetic organic chemistry. In contrast to the reactions involving lithium and magnesium, where the reagents are used in stoichiometric quantities, many of the transition metal reactions will be found to be catalytic processes.

Keywords

Oxidative Addition Aryl Halide Grignard Reagent Phosphine Ligand Conjugate Addition 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

General References

  1. H. Alper (ed.), Transition Metal Organometallics in Organic Synthesis, Vols. I and II, Academic Press, New York, 1978.Google Scholar
  2. J. P. Collman, L. S. Hegedus, J. R. Norton, and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, California, 1987.Google Scholar
  3. H. M. Colquhoun, J. Holton, D. J. Thomson, and M. V. Twigg, New Pathways for Organic Synthesis, Plenum, New York, 1984.CrossRefGoogle Scholar
  4. S. G. Davies, Organo-Transition Metal Chemistry: Applications to Organic Synthesis, Pergamon, Oxford, 1982.Google Scholar
  5. J. K. Kochi, Organometallic Mechanisms and Catalysis, Academic Press, New York, 1979.Google Scholar
  6. E. Negishi, Organometallics in Organic Synthesis, Wiley, New York, 1980.Google Scholar
  7. M. Tsutsui, M. N. Levy, A. Nakamura, M. Ichikawa, and K. Mori, Introduction to Metal π-Complex Chemistry, Plenum, New York, 1970.Google Scholar

Organocopper Reactions

  1. G. Posner, Org. React. 19, 1 (1972).Google Scholar
  2. G. Posner, Org. React. 22, 253 (1975).Google Scholar
  3. G. Posner, An Introduction to Synthesis Using Organocopper Reagents, Wiley-Interscience, New York, 1975.Google Scholar

Organopalladium Reactions

  1. R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, Orlando, Florida, 1985.Google Scholar
  2. R. F. Heck, Org. React. 27, 345 (1982).Google Scholar
  3. J. Tsuji, Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, 1980.CrossRefGoogle Scholar
  4. 1a.
    C. Huynh, F. Derguini-Boumechal, and G. Linstrumelle, Tetrahedron Lett, 1503 (1979).Google Scholar
  5. b.
    N. J. LaLima, Jr., and A. B. Levy, Jr., J. Org. Chem. 43, 1279 (1978).CrossRefGoogle Scholar
  6. c.
    A. Cowell and J. K. Stille, J. Am. Chem. Soc. 102, 4193 (1980).CrossRefGoogle Scholar
  7. d.
    T. Sato, M. Kawasima, and T. Fujisawa, Tetrahedron Lett, 2375 (1981).Google Scholar
  8. e.
    H. P. Dang and G. Linstrumelle, Tetrahedron Lett, 191 (1978).Google Scholar
  9. f.
    B. M. Trost and D. P. Curran, J. Am. Chem. Soc. 102, 5699 (1980).CrossRefGoogle Scholar
  10. g.
    D. J. Pasto, S.-K. Chou, E. Fritzen, R. H. Shults, A. Waterhouse, and G. F. Hennion, J. Org. Chem. 43, 1389 (1978).CrossRefGoogle Scholar
  11. h.
    B. H. Lipshutz, J. Kozlowski, and R. S. Wilhelm, J. Am. Chem. Soc. 104, 2305 (1982).CrossRefGoogle Scholar
  12. i.
    P. A. Grieco and C. V. Srinivasan, J. Org. Chem. 46, 2591 (1981).CrossRefGoogle Scholar
  13. j.
    C. Iwata, K. Suzuki, S. Aoki, K. Okamura, M. Yamashita, I. Takahashi, and T. Tanaka, Chem. Pharm. Bull. 34, 4939 (1988).Google Scholar
  14. k.
    A. Alexakis, G. Cahiez, and J. F. Normant, Org. Synth. 62, 1 (1984).Google Scholar
  15. 1.
    J. Tsuji, Y. Kobayashi, H. Kataoka, and T. Takahashi, Tetrahedron Lett. 21, 1475 (1980).CrossRefGoogle Scholar
  16. m.
    W. A. Nugent and R. J. McKinney, J. Org. Chem. 50, 5370 (1985).CrossRefGoogle Scholar
  17. n.
    R. M. Wilson, K. A. Schnapp, R. K. Merwin, R. Ranganathan, D. L. Moats, and T. T. Conrad, J. Org. Chem. 51, 4028 (1986).CrossRefGoogle Scholar
  18. o.
    L. N. Pridgen, J. Org. Chem. 47, 4319 (1982).CrossRefGoogle Scholar
  19. 2a.
    B. H. Lipshutz, M. Koerner, and D. A. Parker, Tetrahedron Lett. 28, 945 (1987).CrossRefGoogle Scholar
  20. b.
    B. H. Lipshutz, R. S. Wilheim, J. A. Kozlowski, and D. Parker, J. Org. Chem. 49, 3928 (1984).CrossRefGoogle Scholar
  21. c.
    J. P. Marino, R. Fernandez de la Pradilla, and E. Laborde, J. Org. Chem. 52, 4898 (1987).CrossRefGoogle Scholar
  22. d.
    C. R. Johnson and D. S. Dhanoa, J. Org. Chem. 52, 1887 (1987).Google Scholar
  23. 3a.
    H. Urata, A. Fujita, and T. Fuchikami, Tetrahedron Lett. 29, 4435 (1988).CrossRefGoogle Scholar
  24. b.
    Y. Itoh, H. Aoyama, T. Hirao, A. Mochizuki, and T. Saegusa, J. Am. Chem. Soc. 101, 494 (1979).CrossRefGoogle Scholar
  25. c.
    P. G. M. Wuts, M. L. Obrzut, and P. A. Thompson, Tetrahedron Lett. 25, 4051 (1984).CrossRefGoogle Scholar
  26. 4a.
    R. J. Anderson, V. L. Corbin, G. Cotterrel, G. R. Cox, C. A. Henrick, F. Schaub, and J. B. Siddall, J. Am. Chem. Soc. 97, 1197 (1975).CrossRefGoogle Scholar
  27. b.
    P. deMayo, L. K. Sydnes, and G. Wenska, J. Org. Chem. 45, 1549 (1980).CrossRefGoogle Scholar
  28. c.
    Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Org. Chem. 44, 1744 (1979).CrossRefGoogle Scholar
  29. d.
    H. Shostarez and L. A. Paquette, J. Am. Chem. Soc. 103, 722 (1981).CrossRefGoogle Scholar
  30. e.
    W. G. Dauben, G. H. Beasley, M. D. Broadhurst, B. Müller, D. J. Peppard, P. Pesnelle, and C. Suter, J. Am. Chem. Soc. 97, 4973 (1975).CrossRefGoogle Scholar
  31. f.
    L. Watts, J. D. Fitzpatrick, and R. Pettit, J. Am. Chem. Soc. 88, 623 (1966).CrossRefGoogle Scholar
  32. g.
    J. I. Kim, B. A. Patel, and R. F. Heck, J. Org. Chem. 46, 1067 (1981).CrossRefGoogle Scholar
  33. h.
    J. A. Marshall, W. F. Huffman, and J. A. Ruth, J. Am. Chem. Soc. 94, 4691 (1972).CrossRefGoogle Scholar
  34. i.
    H.-A. Hasseberg and H. Gerlach, Helv. Chim. Acta 71, 957 (1988).CrossRefGoogle Scholar
  35. 5a, b.
    B. O’Connor and G. Just, J. Org. Chem. 52, 1801 (1987); G. Just and B. O’Connor, Tetrahedron Lett. 26, 1799 (1985).CrossRefGoogle Scholar
  36. 6.
    B. H. Lipshutz, R. S. Wilheim, J. A. Kozlowski, and D. Parker, J. Org. Chem. 49, 3928 (1984); E. C. Ashby, R. N. DePriest, A. Tuncay, and S. Srivasta, Tetrahedron Lett. 23, 5251 (1982).CrossRefGoogle Scholar
  37. 7a.
    C. G. Chavdarian and C. H. Heathcock, J. Am. Chem. Soc. 97, 3822 (1975).CrossRefGoogle Scholar
  38. b.
    E. J. Corey and D. R. Williams, Tetrahedron Lett., 3847 (1977).Google Scholar
  39. c.
    G. Mehta and K. S. Rao, J. Am. Chem. Soc. 108, 8015 (1986).CrossRefGoogle Scholar
  40. 8a.
    C. M. Lentz and G. H. Posner, Tetrahedron Lett., 3769 (1978).Google Scholar
  41. b.
    A. Marfat, P. R. McGuirk, R. Kramer, and P. Helquist, J. Am. Chem. Soc. 99, 253 (1977).CrossRefGoogle Scholar
  42. c.
    L. A. Paquette and Y.-K. Han, J. Am. Chem. Soc. 103, 1831 (1981).CrossRefGoogle Scholar
  43. d.
    A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett. 27, 1047 (1986).CrossRefGoogle Scholar
  44. e.
    M. Sletzinger, T. R. Verhoeven, R. P. Volante, J. M. McNamara, E. G. Corley, and T. M. H. Liu, Tetrahedron Lett. 26, 2951 (1985).CrossRefGoogle Scholar
  45. 9a.
    E. J. Corey and E. Hamanaka, J. Am. Chem. Soc. 89, 2758 (1967).CrossRefGoogle Scholar
  46. b.
    Y. Kitagawa, A. Itoh, S. Hashimoto, H. Yamamoto, and H. Zozaki, J. Am. Chem. Soc. 99, 3864 (1977).CrossRefGoogle Scholar
  47. c.
    B. M. Trost and R. W. Warner, J. Am. Chem. Soc. 105, 5940 (1983).CrossRefGoogle Scholar
  48. d.
    S. Brandt, A. Marfat, and P. Helquist, Tetrahedron Lett., 2193 (1979).Google Scholar
  49. 10.
    R. H. Grubbs and R. A. Grey, J. Am. Chem. Soc. 95, 5765 (1973).CrossRefGoogle Scholar
  50. 11.
    H. L. Goering, E. P. Seitz, Jr., and C. C. Tseng, J. Org. Chem. 46, 5304 (1981).CrossRefGoogle Scholar
  51. 12.
    A. Marfat, P. R. McGuirk, and P. Helquist, J. Org. Chem. 44, 1345 (1979).CrossRefGoogle Scholar
  52. 13.
    N. Cohen, W. F. Eichel, R. J. Lopresti, C. Neukom, and G. Saucy, J. Org. Chem. 41, 3505 (1976).CrossRefGoogle Scholar
  53. 14a.
    R. J. Linderman, A. Godfrey, and K. Home, Tetrahedron Lett. 28, 3911 (1987).CrossRefGoogle Scholar
  54. b.
    H. Schostarez and L. A. Paquette, J. Am. Chem. Soc. 103, 722 (1981).CrossRefGoogle Scholar
  55. c.
    Y. Yamamoto, S. Yamamoto, H. Yatagai, Y. Ishihara, and K. Maruyam, J. Org. Chem. 47, 119 (1982).CrossRefGoogle Scholar
  56. d.
    T. Kawabata, P. A. Grieco, H.-L. Sham, H. Kim, J. Y. Jaw, and S. Tu, J. Org. Chem. 52, 3346 (1987).CrossRefGoogle Scholar
  57. 15a.
    A. Minato, K. Suzuki, K. Tamao, and M. Kumada, Tetrahedron Lett. 25, 83 (1984).CrossRefGoogle Scholar
  58. b.
    E. R. Larson and R. A. Raphael, Tetrahedron Lett., 5401 (1979).Google Scholar
  59. c.
    M. C. Pirrung and S. A. Thomson, J. Org. Chem. 53, 227 (1988).CrossRefGoogle Scholar
  60. d.
    J. Just and B. O’Connor, Tetrahedron Lett. 29, 753 (1988).CrossRefGoogle Scholar
  61. e.
    M. F. Semmelhack and A. Yamashita, J. Am. Chem. Soc. 102, 5924 (1980).CrossRefGoogle Scholar
  62. f.
    A. M. Echavarren and J. K. Stille, J. Am. Chem. Soc. 110, 4051 (1988).CrossRefGoogle Scholar
  63. 16a.
    J. E. Bäckvall, S. E. Byström, and R. E. Nordberg, J. Org. Chem. 49, 4619 (1984).CrossRefGoogle Scholar
  64. b.
    M. F. Semmelhack and C. Bodurow, J. Am. Chem. Soc. 106, 1496 (1984).CrossRefGoogle Scholar
  65. c.
    D. Valentine, Jr., J. W. Tilley, and R. A. Le Mahieu, J. Org. Chem. 46, 4614 (1981).CrossRefGoogle Scholar
  66. d.
    A. S. Kende, B. Roth, P. J. San Filippo, and T. J. Blacklock, J. Am. Chem. Soc. 104, 5808 (1982).CrossRefGoogle Scholar
  67. 17a.
    P. A. Bartlett, J. D. Meadows, and E. Ottow, J. Am. Chem. Soc. 106, 5304 (1984).CrossRefGoogle Scholar
  68. b.
    M. Larcheveque and Y. Petit, Tetrahedron Lett. 28, 1993 (1987).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Francis A. Carey
    • 1
  • Richard J. Sundberg
    • 1
  1. 1.University of VirginiaCharlottesvilleUSA

Personalised recommendations