Skip to main content

Reactions Involving the Transition Metals

  • Chapter

Part of the book series: Advanced Organic Chemistry ((AOCB))

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.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   74.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

General References

  • H. Alper (ed.), Transition Metal Organometallics in Organic Synthesis, Vols. I and II, Academic Press, New York, 1978.

    Google Scholar 

  • 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 

  • H. M. Colquhoun, J. Holton, D. J. Thomson, and M. V. Twigg, New Pathways for Organic Synthesis, Plenum, New York, 1984.

    Book  Google Scholar 

  • S. G. Davies, Organo-Transition Metal Chemistry: Applications to Organic Synthesis, Pergamon, Oxford, 1982.

    Google Scholar 

  • J. K. Kochi, Organometallic Mechanisms and Catalysis, Academic Press, New York, 1979.

    Google Scholar 

  • E. Negishi, Organometallics in Organic Synthesis, Wiley, New York, 1980.

    Google Scholar 

  • 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

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).

    CAS  Google Scholar 

  3. J. Tsuji, Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, 1980.

    Book  Google Scholar 

  4. C. Huynh, F. Derguini-Boumechal, and G. Linstrumelle, Tetrahedron Lett, 1503 (1979).

    Google Scholar 

  5. N. J. LaLima, Jr., and A. B. Levy, Jr., J. Org. Chem. 43, 1279 (1978).

    Article  CAS  Google Scholar 

  6. A. Cowell and J. K. Stille, J. Am. Chem. Soc. 102, 4193 (1980).

    Article  CAS  Google Scholar 

  7. T. Sato, M. Kawasima, and T. Fujisawa, Tetrahedron Lett, 2375 (1981).

    Google Scholar 

  8. H. P. Dang and G. Linstrumelle, Tetrahedron Lett, 191 (1978).

    Google Scholar 

  9. B. M. Trost and D. P. Curran, J. Am. Chem. Soc. 102, 5699 (1980).

    Article  CAS  Google Scholar 

  10. D. J. Pasto, S.-K. Chou, E. Fritzen, R. H. Shults, A. Waterhouse, and G. F. Hennion, J. Org. Chem. 43, 1389 (1978).

    Article  CAS  Google Scholar 

  11. B. H. Lipshutz, J. Kozlowski, and R. S. Wilhelm, J. Am. Chem. Soc. 104, 2305 (1982).

    Article  CAS  Google Scholar 

  12. P. A. Grieco and C. V. Srinivasan, J. Org. Chem. 46, 2591 (1981).

    Article  CAS  Google Scholar 

  13. C. Iwata, K. Suzuki, S. Aoki, K. Okamura, M. Yamashita, I. Takahashi, and T. Tanaka, Chem. Pharm. Bull. 34, 4939 (1988).

    Google Scholar 

  14. A. Alexakis, G. Cahiez, and J. F. Normant, Org. Synth. 62, 1 (1984).

    CAS  Google Scholar 

  15. J. Tsuji, Y. Kobayashi, H. Kataoka, and T. Takahashi, Tetrahedron Lett. 21, 1475 (1980).

    Article  CAS  Google Scholar 

  16. W. A. Nugent and R. J. McKinney, J. Org. Chem. 50, 5370 (1985).

    Article  CAS  Google Scholar 

  17. R. M. Wilson, K. A. Schnapp, R. K. Merwin, R. Ranganathan, D. L. Moats, and T. T. Conrad, J. Org. Chem. 51, 4028 (1986).

    Article  CAS  Google Scholar 

  18. L. N. Pridgen, J. Org. Chem. 47, 4319 (1982).

    Article  CAS  Google Scholar 

  19. B. H. Lipshutz, M. Koerner, and D. A. Parker, Tetrahedron Lett. 28, 945 (1987).

    Article  CAS  Google Scholar 

  20. B. H. Lipshutz, R. S. Wilheim, J. A. Kozlowski, and D. Parker, J. Org. Chem. 49, 3928 (1984).

    Article  CAS  Google Scholar 

  21. J. P. Marino, R. Fernandez de la Pradilla, and E. Laborde, J. Org. Chem. 52, 4898 (1987).

    Article  CAS  Google Scholar 

  22. C. R. Johnson and D. S. Dhanoa, J. Org. Chem. 52, 1887 (1987).

    Google Scholar 

  23. H. Urata, A. Fujita, and T. Fuchikami, Tetrahedron Lett. 29, 4435 (1988).

    Article  CAS  Google Scholar 

  24. Y. Itoh, H. Aoyama, T. Hirao, A. Mochizuki, and T. Saegusa, J. Am. Chem. Soc. 101, 494 (1979).

    Article  Google Scholar 

  25. P. G. M. Wuts, M. L. Obrzut, and P. A. Thompson, Tetrahedron Lett. 25, 4051 (1984).

    Article  CAS  Google Scholar 

  26. 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).

    Article  CAS  Google Scholar 

  27. P. deMayo, L. K. Sydnes, and G. Wenska, J. Org. Chem. 45, 1549 (1980).

    Article  CAS  Google Scholar 

  28. Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Org. Chem. 44, 1744 (1979).

    Article  CAS  Google Scholar 

  29. H. Shostarez and L. A. Paquette, J. Am. Chem. Soc. 103, 722 (1981).

    Article  Google Scholar 

  30. 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).

    Article  CAS  Google Scholar 

  31. L. Watts, J. D. Fitzpatrick, and R. Pettit, J. Am. Chem. Soc. 88, 623 (1966).

    Article  CAS  Google Scholar 

  32. J. I. Kim, B. A. Patel, and R. F. Heck, J. Org. Chem. 46, 1067 (1981).

    Article  CAS  Google Scholar 

  33. J. A. Marshall, W. F. Huffman, and J. A. Ruth, J. Am. Chem. Soc. 94, 4691 (1972).

    Article  CAS  Google Scholar 

  34. H.-A. Hasseberg and H. Gerlach, Helv. Chim. Acta 71, 957 (1988).

    Article  CAS  Google Scholar 

  35. B. O’Connor and G. Just, J. Org. Chem. 52, 1801 (1987); G. Just and B. O’Connor, Tetrahedron Lett. 26, 1799 (1985).

    Article  Google Scholar 

  36. 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).

    Article  CAS  Google Scholar 

  37. C. G. Chavdarian and C. H. Heathcock, J. Am. Chem. Soc. 97, 3822 (1975).

    Article  CAS  Google Scholar 

  38. E. J. Corey and D. R. Williams, Tetrahedron Lett., 3847 (1977).

    Google Scholar 

  39. G. Mehta and K. S. Rao, J. Am. Chem. Soc. 108, 8015 (1986).

    Article  CAS  Google Scholar 

  40. C. M. Lentz and G. H. Posner, Tetrahedron Lett., 3769 (1978).

    Google Scholar 

  41. A. Marfat, P. R. McGuirk, R. Kramer, and P. Helquist, J. Am. Chem. Soc. 99, 253 (1977).

    Article  CAS  Google Scholar 

  42. L. A. Paquette and Y.-K. Han, J. Am. Chem. Soc. 103, 1831 (1981).

    Article  CAS  Google Scholar 

  43. A. Alexakis, J. Berlan, and Y. Besace, Tetrahedron Lett. 27, 1047 (1986).

    Article  CAS  Google Scholar 

  44. M. Sletzinger, T. R. Verhoeven, R. P. Volante, J. M. McNamara, E. G. Corley, and T. M. H. Liu, Tetrahedron Lett. 26, 2951 (1985).

    Article  CAS  Google Scholar 

  45. E. J. Corey and E. Hamanaka, J. Am. Chem. Soc. 89, 2758 (1967).

    Article  CAS  Google Scholar 

  46. Y. Kitagawa, A. Itoh, S. Hashimoto, H. Yamamoto, and H. Zozaki, J. Am. Chem. Soc. 99, 3864 (1977).

    Article  CAS  Google Scholar 

  47. B. M. Trost and R. W. Warner, J. Am. Chem. Soc. 105, 5940 (1983).

    Article  CAS  Google Scholar 

  48. S. Brandt, A. Marfat, and P. Helquist, Tetrahedron Lett., 2193 (1979).

    Google Scholar 

  49. R. H. Grubbs and R. A. Grey, J. Am. Chem. Soc. 95, 5765 (1973).

    Article  CAS  Google Scholar 

  50. H. L. Goering, E. P. Seitz, Jr., and C. C. Tseng, J. Org. Chem. 46, 5304 (1981).

    Article  CAS  Google Scholar 

  51. A. Marfat, P. R. McGuirk, and P. Helquist, J. Org. Chem. 44, 1345 (1979).

    Article  CAS  Google Scholar 

  52. N. Cohen, W. F. Eichel, R. J. Lopresti, C. Neukom, and G. Saucy, J. Org. Chem. 41, 3505 (1976).

    Article  CAS  Google Scholar 

  53. R. J. Linderman, A. Godfrey, and K. Home, Tetrahedron Lett. 28, 3911 (1987).

    Article  CAS  Google Scholar 

  54. H. Schostarez and L. A. Paquette, J. Am. Chem. Soc. 103, 722 (1981).

    Article  CAS  Google Scholar 

  55. Y. Yamamoto, S. Yamamoto, H. Yatagai, Y. Ishihara, and K. Maruyam, J. Org. Chem. 47, 119 (1982).

    Article  CAS  Google Scholar 

  56. T. Kawabata, P. A. Grieco, H.-L. Sham, H. Kim, J. Y. Jaw, and S. Tu, J. Org. Chem. 52, 3346 (1987).

    Article  CAS  Google Scholar 

  57. A. Minato, K. Suzuki, K. Tamao, and M. Kumada, Tetrahedron Lett. 25, 83 (1984).

    Article  CAS  Google Scholar 

  58. E. R. Larson and R. A. Raphael, Tetrahedron Lett., 5401 (1979).

    Google Scholar 

  59. M. C. Pirrung and S. A. Thomson, J. Org. Chem. 53, 227 (1988).

    Article  CAS  Google Scholar 

  60. J. Just and B. O’Connor, Tetrahedron Lett. 29, 753 (1988).

    Article  CAS  Google Scholar 

  61. M. F. Semmelhack and A. Yamashita, J. Am. Chem. Soc. 102, 5924 (1980).

    Article  CAS  Google Scholar 

  62. A. M. Echavarren and J. K. Stille, J. Am. Chem. Soc. 110, 4051 (1988).

    Article  CAS  Google Scholar 

  63. J. E. Bäckvall, S. E. Byström, and R. E. Nordberg, J. Org. Chem. 49, 4619 (1984).

    Article  Google Scholar 

  64. M. F. Semmelhack and C. Bodurow, J. Am. Chem. Soc. 106, 1496 (1984).

    Article  CAS  Google Scholar 

  65. D. Valentine, Jr., J. W. Tilley, and R. A. Le Mahieu, J. Org. Chem. 46, 4614 (1981).

    Article  CAS  Google Scholar 

  66. A. S. Kende, B. Roth, P. J. San Filippo, and T. J. Blacklock, J. Am. Chem. Soc. 104, 5808 (1982).

    Article  CAS  Google Scholar 

  67. P. A. Bartlett, J. D. Meadows, and E. Ottow, J. Am. Chem. Soc. 106, 5304 (1984).

    Article  CAS  Google Scholar 

  68. M. Larcheveque and Y. Petit, Tetrahedron Lett. 28, 1993 (1987).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Plenum Press, New York

About this chapter

Cite this chapter

Carey, F.A., Sundberg, R.J. (1990). Reactions Involving the Transition Metals. In: Advanced Organic Chemistry. Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-9797-7_8

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-9797-7_8

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-43457-0

  • Online ISBN: 978-1-4613-9797-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics