Carbonylation Reactions of Organic Halides by Tetrakis(Triphenylphosphine)Nickel (O) and Palladium (O) Carbonyl Complexes under Mild Conditions

  • Masanobu Hidai
  • Yasuzo Uchida
  • Ikuei Ogata


Synthesis of carboxylic acids and esters by carbonylation reactions at atmospheric pressure using transition metal catalysts is currently receiving considerable attention and has recently been reviewed by Cassar, Chiusoli, and Guerrieri.1 Nickel-thiourea complexes,2 nickel tetracarbonyl,3 cobalt carbonyl anion,4 and an iodide-promoted rhodium compound5 are, for example, used for carbonylation reactions of organic halides under mild conditions. Coordination of carbon monoxide to metals (metal carbonyl complexes), oxidative additon of organic halides to low-valent transition metal complexes with the formation of carbon-metal bonds, and insertion of carbon monoxide into carbon-metal bonds with the formation of acyl complexes are important elementary processes involved in these reactions. We wish here to report the recent results of the study on carbonylation reactions of organic halides by tetrakis(triphenylphosphine)nickel (O) and palladium (O) carbonyl complexes under mild conditions.6


Benzoyl Chloride Methyl Benzoate Carbonyl Complex Carbonylation Reaction Allyl Chloride 


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  1. 1.
    L. Cassar, G. P. Chiusoli, and F. Guerrieri, Synthesis, 509 (1973).Google Scholar
  2. 2.(a)
    G. P. Chiusoli, S. Merzoni, and G. Mondelli, Chimica e Industria, 47, 743 (1965);Google Scholar
  3. (b).
    G. P. Chiusoli, M. Dubini, M. Ferraris, F. Guerrieri, S. Merzoni, and G. Mondelli, J. Chem. Soc. C, 2889 (1968).Google Scholar
  4. 3.(a)
    L. Cassar and M. Foa, Inorg. Nucl. Chem. Letters, 6, 291 (1970);CrossRefGoogle Scholar
  5. (b).
    E. J. Corey and L. S. Hegedus, J. Amer. Chem. Soc., 91, 1233 (1969);CrossRefGoogle Scholar
  6. (c).
    M. Nakayama and T. Mizoroki, Bull. Chem. Soc. Japan, 44, 508 (1971);CrossRefGoogle Scholar
  7. (d).
    L. Cassar and M. Foa, J. Organo-metal. Chem., 51, 381 (1973).CrossRefGoogle Scholar
  8. 4.
    R. F. Heck in Organic Synthesis via Metal Carbonyls Vol. II, I Wender and P. Pino Ed., Interscience, New York, 1968.Google Scholar
  9. 5.
    J. F. Roth and J. H. Craddock, Abstracts of Papers, 162nd National Meeting of the American Chemical Society, Washington, 12–17, September, 1971.Google Scholar
  10. 6.
    M, Hidai, Y. Wada, S. Uzawa, Y. Uchida, I. Ogata, and K. Nobuchika, A part of this paper presented at the 30th Annual Meeting of the Chemical Society of Japan, April 1974, Osaka.Google Scholar
  11. 7.
    M. Hidai, T. Kashiwagi, T. Ikeuchi, and Y. Uchida, J. Organometal, Chem., 30, 279 (1971).CrossRefGoogle Scholar
  12. 8.
    S. Otsuka, A. Nakamura, T. Yoshida, M. Naruto, and K. Ataka, J. Amer. Chem. Soc., 95, 3180 (1973).CrossRefGoogle Scholar
  13. 9.
    H. F. Klein, Angew. Chem. Internat. Edit., 12, 402 (1973).CrossRefGoogle Scholar
  14. 10.
    S. Otsuka and I, Kato, to be published.Google Scholar
  15. 11.
    J, B. Hendrickson, D, J. Cram, and G. S. Hammond, Organic Chemistry, McGraw-Hill, New York, 3rd ed., 304 (1970).Google Scholar
  16. 12.(a)
    K. Kudo, M, Hidai, and Y. Uchida, J. Organometal. Chem., 33, 393 (1971);CrossRefGoogle Scholar
  17. (b).
    M. Hidai, M, Kokura, and Y. Uchida, ibid., 52, 431 (1973).Google Scholar
  18. 13.
    P. Fitton, M. P. Johnson, and J. E. McKeon, Chem. Comm., 6 (1968).Google Scholar
  19. 14.
    G, Booth and J, Chatt, J. Chem. Soc. A, 634 (1966).Google Scholar
  20. 15.
    K. Kudo, M. Sato, M, Hidai, and Y. Uchida, Bull. Chem. Soc. Japan, 46, 2820 (1973).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1975

Authors and Affiliations

  • Masanobu Hidai
    • 1
    • 2
  • Yasuzo Uchida
    • 1
    • 2
  • Ikuei Ogata
    • 1
    • 2
  1. 1.Department of Industrial ChemistryUniversity of TokyoHongo, TokyoJapan
  2. 2.National Chemical Laboratory for IndustryHonmachi, Shibuya-ku, TokyoJapan

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