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Organometallic Compounds of the Group I, II, and III Metals

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Part B: Reactions and Synthesis

Part of the book series: Advanced Organic Chemistry ((AOC,volume Pt. B))

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Abstract

The use of organometallic reagents in organic synthesis had its beginning around 1900 when Victor Grignard discovered that alkyl and aryl halides react with magnesium metal to give homogeneous solutions containing organomagnesium compounds. The “Grignard reagents” proved to be highly reactive carbon nucleophiles and have remained very useful synthetic reagents since that time. Organolithium reagents came into synthetic use somewhat later. This chapter will focus primarily on Grignard reagents and organolithium compounds. These reagents are highly reactive carbon nucleophiles with fundamental applications in organic synthesis. We will also consider zinc, cadmium, mercury, indium, and lanthanide organometallics. Each of these classes of compounds has more specialized places in synthetic methodology. Certain of the transition metals, such as copper, palladium, and nickel, are important in synthetic methodology and will be discussed in Chapter 8.

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General References

  • E. Erdik, Organozinc Reagents in Organic Synthesis, CRC Press, Boca Raton, Florida, 1996.

    Google Scholar 

  • P. Knochel and P. Jones, editors, Organic Zinc Reagents. A Practical Approach, Oxford University Press, Oxford, UK, 1999.

    Google Scholar 

  • P. R. Jenkins, Organometallic Reagents in Synthesis, Oxford University Press, Oxford, UK, 1992.

    Google Scholar 

  • R. C. Larock, Organomercury Compounds in Organic Synthesis, Springer Verlag, Berlin, 1985.

    Book  Google Scholar 

  • M. Schlosser, editor, Organometallic in Synthesis; A Manual, Wiley, New York, 1994.

    Google Scholar 

  • G. S. Silverman and P. E. Rakita, editors, Handbook of Grignard Reagents, Marcel Dekker, New York, 1996.

    Google Scholar 

  • B. J. Wakefield, The Chemistry of Organolithium Compounds, Pergamon, Oxford, 1974.

    Google Scholar 

  • B. J. Wakefield, Organolithium Methods, Academic Press, Orlando, Florida, 1988.

    Google Scholar 

  • B. J. Wakefield, Organomagnesium Methods in Organic Synthesis, Academic Press, London, 1995.

    Google Scholar 

Chapter 7

  1. H. Neumann and D. Seebach, Tetrahedron Lett. 1976:4839.

    Google Scholar 

  2. P. Canonne, G. Foscolos, and G. Lemay, Tetrahedron Lett. 1980:155.

    Google Scholar 

  3. T. L. Shih, M. Wyvratt, and H. Mrozik, J. Org. Chem. 52:2029 (1987).

    Article  CAS  Google Scholar 

  4. R. K. Boeckman, Jr., and E. W. Thomas, J. Am. Chem. Soc. 101:987 (1979).

    Article  CAS  Google Scholar 

  5. G. M. Rubottom and C. Kim, J. Org. Chem. 48:1550 (1983).

    Article  CAS  Google Scholar 

  6. S. L. Buchwald, B. T. Watson, R. T. Lum, and W. A. Nugent, J. Am. Chem. Soc. 109:7137 (1987).

    Article  Google Scholar 

  7. T. Okazoe, K. Takai, K. Oshima, and K. Utimoto, J. Org. Chem. 52:4410 (1987).

    Article  CAS  Google Scholar 

  8. J. W. Frankenfeld and J. J. Werner, J. Org. Chem. 34:3689 (1969).

    Article  CAS  Google Scholar 

  9. E. R. Burkhardt and R. D. Rieke, J. Org. Chem. 50:416 (1985).

    Article  CAS  Google Scholar 

  10. G. Veeresa and A. Datta, Tetrahedron 54:15673 (1998).

    Article  CAS  Google Scholar 

  11. R. W. Herr and C. R. Johnson, J. Am. Chem. Soc. 92:4979 (1970).

    Article  CAS  Google Scholar 

  12. J. S. Sawyer, A. Kucerovy, T. L. Macdonald, and G. J. McGarvey, J. Am. Chem. Soc. 110:842 (1988).

    Article  CAS  Google Scholar 

  13. T. Cohen and J. R. Matz, J. Am. Chem. Soc. 102:6900 (1980).

    Article  CAS  Google Scholar 

  14. C. R. Johnson and J. R. Medich, J. Org. Chem. 53:4131 (1988).

    Article  CAS  Google Scholar 

  15. B. M. Trost and T. N. Nanninga, J. Am. Chem. Soc. 107:1293 (1985).

    Article  CAS  Google Scholar 

  16. T. Morwick, Tetrahedron Lett. 21:3227 (1980).

    Article  CAS  Google Scholar 

  17. W. C. Still and C. Sreekumar, J. Am. Chem. Soc. 102:1201 (1980).

    Article  CAS  Google Scholar 

  18. R. F. Cunio and F. J. Clayton, J. Org. Chem. 41:1480 (1976).

    Article  Google Scholar 

  19. J. J. Fitt and H. W. Gschwend, J. Org. Chem. 45:4258 (1980).

    Article  Google Scholar 

  20. S. Aikyama and J. Hooz, Tetrahedron Lett. 1973:4115.

    Google Scholar 

  21. K. P. Klein and C. R. Hauser, J. Org. Chem. 32:1479 (1967).

    Article  CAS  Google Scholar 

  22. B. M. Graybill and D. A. Shirley, J. Org. Chem. 31:1221 (1966).

    Article  CAS  Google Scholar 

  23. M. M. Midland, A. Tramontano, and J. R. Cable, J. Org. Chem. 45:28 (1980).

    Article  CAS  Google Scholar 

  24. W. Fuhrer and H. W. Gschwend, J. Org. Chem. 44:1133 (1979).

    Article  CAS  Google Scholar 

  25. D. F. Taber and R. W. Korsmeyer, J. Org. Chem. 43:4925 (1978).

    Article  CAS  Google Scholar 

  26. R. R. Schmidt, J. Talbiersky, and P. Russegger, Tetrahedron Lett. 1979:4273.

    Google Scholar 

  27. R. M. Carlson, Tetrahedron Lett. 1978: 111.

    Google Scholar 

  28. R. J. Sundberg, R. Broome, C. P. Walters, and D. Schnur, J. Heterocycl. Chem. 18:807 (1981).

    Article  CAS  Google Scholar 

  29. J. J. Eisch and J. N. Shah, J. Org. Chem. 56:2955 (1991).

    Article  CAS  Google Scholar 

  30. M. P. Dreyfuss, J. Org. Chem. 28:3269 (1963).

    Article  CAS  Google Scholar 

  31. P. J. Pearce, D. H. Richards, and N. F. Scilly, Org. Synth. 52:19 (1972).

    CAS  Google Scholar 

  32. U. Schöllkopf, H. Küppers, H.-J. Traencker, and W. Pitteroff, Justus Liebigs Ann. Chem. 704:120 (1967).

    Article  Google Scholar 

  33. J. V. Hay and T. M. Harris, Org. Synth. 53:56 (1973).

    CAS  Google Scholar 

  34. F. Sato, M. Inoue, K. Oguro, and M. Sato, Tetrahedron Lett. 1979:4303.

    Google Scholar 

  35. J. C. H. Hwa and H. Sims, Org. Synth. V:608 (1973).

    Google Scholar 

  36. J. H. Rigby and C. Senanyake, J. Am. Chem. Soc. 109:3147 (1987).

    Article  CAS  Google Scholar 

  37. K. Takai, Y. Kataoka, T. Okazoe, and K. Utimoto, Tetrahedron Lett. 29:1065 (1988).

    Article  CAS  Google Scholar 

  38. E. Nakamura, S. Aoki, K. Sekiya, H. Oshino, and I. Kuwajima, J. Am. Chem. Soc. 109:8056 (1987).

    Article  CAS  Google Scholar 

  39. H. A. Whaley, J. Am. Chem. Soc. 93:3767 (1971).

    Article  CAS  Google Scholar 

  40. J. Barluenga, F. J. Fananas, and M. Yus, J. Org. Chem. 44:4798 (1979).

    Article  CAS  Google Scholar 

  41. W. C. Still and J. H. McDonald III, Tetrahedron Lett. 21:1031 (1980).

    Article  CAS  Google Scholar 

  42. E. Casadevall and Y. Povet, Tetrahedron Lett. 1976:2841.

    Google Scholar 

  43. P. Beak, J. E. Hunter, Y. M. Jan, and A. P. Wallin, J. Am. Chem. Soc. 109:5403 (1987).

    Article  CAS  Google Scholar 

  44. C. J. Kowalski and M. S. Haque, J. Org Chem. 50:5140 (1985).

    Article  CAS  Google Scholar 

  45. C. Fehr, J. Galindo, and R. Perret, Helv. Chim. Acta 70:1745 (1987).

    Article  CAS  Google Scholar 

  46. M. P. Cooke, Jr., and I. N. Houpis, Tetrahedron Lett. 26:4987 (1985)

    Article  CAS  Google Scholar 

  47. E. Piers and P. C. Marais, Tetrahedron Lett. 29:4053 (1988).

    Article  CAS  Google Scholar 

  48. C. Phillips, R. Jacobson, B. Abrahams, H. J. Williams, and C. R. Smith, J. Org. Chem. 45:1920 (1980).

    Article  CAS  Google Scholar 

  49. T. Cohen and J. R. Matz, J. Am. Chem. Soc. 102:6900 (1980).

    Article  CAS  Google Scholar 

  50. T. R. Govindachari, P. C. Parthasarathy, H. K. Desai, and K. S. Ramachandran, Indian J. Chem. 13:537 (1975).

    CAS  Google Scholar 

  51. W. C. Still, J. Am. Chem. Soc. 100:1481 (1978).

    Article  CAS  Google Scholar 

  52. E. J. Corey and D. R. Williams, Tetrahedron Lett. 1977:3847.

    Google Scholar 

  53. T. Okazoe, K. Takai, K. Oshiama, and K. Utimoto, J. Org. Chem. 52:4410 (1987).

    Article  CAS  Google Scholar 

  54. M. A. Adams, A. J. Duggan, J. Smolanoff, and J. Meinwald, J. Am. Chem. Soc. 101:5364 (1979).

    Article  CAS  Google Scholar 

  55. S. O. deSilva, M. Watanabe, and V. Snieckus, J. Org. Chem. 44:4802 (1979).

    Article  CAS  Google Scholar 

  56. M. Kitamura, S. Suga, K. Kawai, and R. Noyori, J. Am. Chem. Soc. 108:6071 (1986)

    Article  CAS  Google Scholar 

  57. K. Soai, A. Ookawa, T. Kaba, and K. Ogawa, J. Am. Chem. Soc. 109:7111 (1987)

    Article  CAS  Google Scholar 

  58. M. Kitamura, S. Okada, and R. Noyori, J. Am. Chem. Soc. 111:4028 (1989).

    Article  CAS  Google Scholar 

  59. C. A. Broka and T. Shen, J. Am. Chem. Soc. 111:2981 (1989).

    Article  CAS  Google Scholar 

  60. W.-L. Cheng, Y.-J. Shaw, S.-M. Yeh, P. P. Kanakamma, Y.-H. Chen, C. Chen, J.-C. Shieu, S.-J. Yiin, G.-H. Lee, Y. Wang, and T.-Y. Luh, J. Org. Chem. 64:532 (1999).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. University of Virginia, Charlottesville, Virginia, USA

    Francis A. Carey & Richard J. Sundberg

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  1. Francis A. Carey
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  2. Richard J. Sundberg
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Carey, F.A., Sundberg, R.J. (2001). Organometallic Compounds of the Group I, II, and III Metals. In: Part B: Reactions and Synthesis. Advanced Organic Chemistry, vol Pt. B. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-39510-3_7

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  • DOI: https://doi.org/10.1007/978-3-662-39510-3_7

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-38652-1

  • Online ISBN: 978-3-662-39510-3

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