Phosphine-Nickel Complexes as Catalysts for Cross-Coupling Reaction of Grignard Reagents with Vinylic, Aromatic and Heteroaromatic Halides

  • Makoto Kumada

Abstract

Recently, Corriu and Masse,1 and we2 independently reported the selective carbon-carbon bond formation by cross-coupling of Grignard reagents with olefinic and with aromatic halides in the presence of nickel complexes as catalysts. Here we briefly summarize our own work using various kinds of phosphine-nickel complexes, and consider possible effects of phosphine ligands on the catalytic activity of the nickel atom in both the cross-coupling and secondary reactions.

Keywords

Nickel Acetylene Lide Phosphine Stilbene 

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References

  1. 1.
    R. J. P. Corriu and J. P. Masse, Chem. Comm., 144 (1972). Google Scholar
  2. 2. (a)
    K. Tamao, K. Sumitani and M. Kumada, J. Amer. Chem. Soc., 94, 4374 (1972);CrossRefGoogle Scholar
  3. (b).
    K. Tamao, Y. Kiso, K. Sumitani and M. Kumada, ibid., 94, 9268 (1972);Google Scholar
  4. (c).
    Y. Kiso, K. Tamao and M. Kumada, J. Organometal. Chem., 50, C12 (1973);CrossRefGoogle Scholar
  5. (d).
    K. Tamao, M. Zembayashi, Y. Kiso and M. Kumada, ibid., 55, C91 (1973).Google Scholar
  6. 3.
    P. M. Boorman and A. J. Carty, Inorg. Nucl. Chem. Letters, 4, 101 (1968).CrossRefGoogle Scholar
  7. 4.
    M, Hidai, T. Kashiwagi, T. Ikeuchi and Y. Uchida, J. Organometal. Chem., 30, 279 (1971).CrossRefGoogle Scholar
  8. 5.
    Z. Rappoport, Advan. Phys. Org. Chem., 7, 1 (1969).CrossRefGoogle Scholar
  9. 6 (a).
    Y. Kiso, K. Tamao, N. Miyake, K. Yamamoto and M. Kumada, Tetrahedron Lett., 3 (1974);Google Scholar
  10. (b).
    G. Consiglio and C. Botteghi, Helv. Chirp. Acta, 56, 460 (1973).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1975

Authors and Affiliations

  • Makoto Kumada
    • 1
  1. 1.Department of Synthetic ChemistryKyoto UniversityKyotoJapan

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