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Selective Dehalogenative Homocoupling of Haloarylsulfonates by th Use of Palladium Catalyst


Abstract

The palladium catalyzed dehalogenative homocoupling of haloarylsulfonates under reductive conditions has proceeded selectively depending on the type of the halogen. Thus, an iodo or a bromo leaving group of haloarylsulfonates was homocoupled to gi ve symmetrical biaryls in good yields with the sulfonate group intact, whereas a chloro leaving group gave no reaction under the conditions used. When the more reactive nickel catalyst was employed instead of the palladium catalyst in the reaction, both dehalogenative and desulfonative homocouplings of haloarylsulfonates occurred regardless of the type of the halogen used.

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References

  1. Academic Press Palladium Reagents in Organic Synthesis Heck, R. F.
  2. Synthesis Ritter, K.
  3. Chem. Rev. Grushin, V. V.;Alper, H.
  4. J. Am. Chem. Soc. v.93 Semmalhacj, M. F.lHelquist, P. M.;Jones, L. D.
  5. J. Am. Chem. Soc. v.97 Semmalhacj, M. F.;Ryno, L. S.
  6. J. Am. Chem. Soc. v.103 Semmalhacj, M. F.lHelquist, P. M.;Jones, L. D.;Keller, L.;Mendelsin, L.;Ryno, L. S.;Smith, J. G.;Suauffer, R. D.
  7. Tetrahedron Lett. v.23 Inaba, S. I.;Matsumoto, H.;Rieke, R. D.
  8. J. Chem. Soc., Perkin I Clark, F. R. S.;Norman, R. O. C.;Thomas. C. B.
  9. Tetrahedron Lett. v.39 Luo, F. T.;Jeevanandam, A.;Basu, M. K.
  10. J. Chem. Soc., Perkin I Vananzi, L. M.
  11. Macromolecules v.28 Percec, V.;Bae, J. Y.;Zhao, M.;Hill, D. H.
  12. J. Org. Chem. v.59 Olszewski, J. D.;Marshalla, M.lSabat, M.;Sundberg, R. J.
  13. J. Am. Chem. Soc. v.61 Stewart, E.
  14. Macromolecules v.29 Percec, V.;Zhao, M.;Hill, D. H.
  15. J. Organoment. Chem. v.28 Fitton, P.;Rick, A. E.
  16. J. Am. Chem. Soc. v.93 Gerlach, D. H.;Kane, A. R.;Parshall, G. W.;Jasson, J. R;Muetterties, E. L.
  17. J. Am. Chem. Soc. v.98 Garrou, P. E.;Heck, R. F.
  18. J. Korean Ind. Eng. Chem. v.11 Lee, T. S.;kim, J. H.;Bae, J. Y.