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1887
Volume 37, Issue 1
  • ISSN: 0032-1400

Abstract

The organometallic chemistry of palladium is dominated by the +II oxidation state, and the chemistry of complexes containing simple organic groups bonded to palladium in the +IV oxidation state has developed only recently. Organic synthesis and catalytic reactions that may involve undetected palladium(IV) intermediates have been suggested frequently, and the new oxidation state +IV chemistry provides some support for these proposals, and gives encouragement for the development of new systems involving palladium(IV). The chemistry of organopalladium(IV) is reviewed here, and possible catalytic roles forpalladium(IV) are discussed. The synthesis and decomposition reactions of palladium(IV) complexes provide “models” for catalytic proposals. The palladium(IV) complexes are formed by oxidative addition of organohalides to palladium(II) complexes, and most complexes decompose under mild conditions by carbon-carbon bond formation in reductive elimination reactions, for example, for methyl(pheny1) (2,2’-bipyridyl)palladium(II) as a substrate, oxidative addition of benzyl bromide gives PdIV BrMePh(CHPh) (bpy), which reductively eliminates toluene to form the complex PdIIBr(CHPh)(bpy).

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1993-01-01
2024-09-27
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References

  1. R. F. Heck, Palladium Reagents in Organic Synthesis”, Academic, New York, 1985 [Google Scholar]
  2. D. Milstein, J. K. Stille, J. Am. Chem. Soc., 1979, 101, 4992; (b) [Google Scholar]
  3. A. Gillie, J. K. Stille, J. Am. Chem. Soc., 1980, 102, 4933; (c) [Google Scholar]
  4. M. K. Loar, J. K. Stille, J. Am. Chem. Soc., 1981, 103, 4174; (d) [Google Scholar]
  5. R. A. Holton, K. J. Natalie, Tetrahedron Lew, 1981, 22, 267; (e) [Google Scholar]
  6. S. J. Tremont, H. U. Rahman, J Am. Chem. Soc., 1984, 106, 5759; (f) [Google Scholar]
  7. F. Maassarani, M. Pfeffer, G. Le Borgne, J. T. B. H. Jastrzebski, G. van Koten, Organometallics, 1987, 6, 1111; (g) [Google Scholar]
  8. M. Catellani, G. P. Chiusoli, J. Organomet. Chem., 1988, 346, C27; (h) [Google Scholar]
  9. M. Catellani, G. P. Chiusoli, M. Costa, PureAppl. Chem., 1990, 62, 623; (i) [Google Scholar]
  10. H. Kurosawa, M. Emoto, Y. Kawasaki, J. Organomet. Chem., 1988, 346, 137; (j) [Google Scholar]
  11. O. Reiser, M. Weber, A. de Meijere, Angevi. Chem. Int. Ed. Engl., 1989, 28, 1037; (k) [Google Scholar]
  12. A. Albinati, S. Affolter, P. S. Pregosin, J. Organomet. Chem., 1990, 395, 231 [Google Scholar]
  13. A. D. Ketley, L. P. Fisher, A. J. Berlin, C. R. Morgan, E. H. Gorman, T. R. Steadman, Inorg. Chem., 1967, 6, 657; (b) [Google Scholar]
  14. P. M. Henry, Acc. Chem. Res., 1973, 6, 16; (c) [Google Scholar]
  15. G. Oehme, J. Prakt. Chem., 1984, 326, 779; (d) [Google Scholar]
  16. R. P. Thummel, Y. Jahng, J. Org. Chem., 1987, 52, 73; (e) [Google Scholar]
  17. A. D. Ryabov, A. V. Eliseev, A. K. Yatsimirsky, Appl. Organomet. Chem., 1988, 2, 101; (f) [Google Scholar]
  18. B. M. Trost, Acc Chem. Res., 1990, 23, 34; (g) [Google Scholar]
  19. I. Guibert, D. Neibecker, I. Tkatchenko, J. Chem. Soc, Chem. Commun., 1989, 1850 [Google Scholar]
  20. R. Uson, J. Fornies, R. Navarro, J. Organomet. Chem., 1975, 96, 307, Synth. React. Inorg. Met.-Org. Chem., 1977, 7, 235 [Google Scholar]
  21. P. K. Byers, A. J. Canty, B. W. Skelton, A. H. White, J. Chem. Soc, Chem. Commun., 1986, 1722 [Google Scholar]
  22. W. de Graaf, J. Boersma, W. J. J. Smeets, A. L. Spek, G. van Koten, Organometallics, 1989, 8, 2907; (b) [Google Scholar]
  23. W. de Graaf, J. Boersma, G. van Koten, Organometallics, 1990, 9, 1479 [Google Scholar]
  24. M. Catellani, B. E. Mann, J. Organomet. Chem., 1990, 390, 251 [Google Scholar]
  25. A. J. Canty, Acc. Chem. Res., 1992, 25, 83 [Google Scholar]
  26. A. J. Canty, P. R. Traill, B. W. Skelton, A. H. White, ibid., Ref. 7, 1991, 402, C33; and 1992, 433, 213
  27. P. K. Byers, A. J. Canty, P. R. Traill, A. A. Watson, J. Organomet. Chem., 1990, 390, 399 [Google Scholar]
  28. B. A. Markies, A. J. Canty, M. D. Janssen, A. L. Spek, J. Boersma, G. van Koten, Red. Trav. Chim. Pays Bas, 1991, 110, 477 [Google Scholar]
  29. M. A. Bennett, A. J. Canty, J. Felixberger, L. M. Rendina, C. Sunderland, A. C. Willis,
  30. P.K. Byers, A.J. Canty, R.J. Puddephatt, J. D. Scott, ibid., Ref. 6, 1988, 7, 1363; (b)
  31. K-T. Aye, A. J. Canty, M. Crespo, R. J. Rridephatt, J. D. Scott, A. A. Watson, op. at., 1989, 8, 1518
  32. A. J. Canty, A. A. Watson, B. W. Skelton, A. H. White, J. Organomet. Chem., 1989, 367, C25 [Google Scholar]
  33. J. M. Brown, N. A. Cooley, Chem. Rev., 1988, 88, 1031 [Google Scholar]
  34. J. V. Ortiz, Z. Havlas, R. Hoffmann, Helv. Chim. Acta, 1984, 67, 1; (b) [Google Scholar]
  35. J. Terheijden, G. van Koten, I. C. Vinke, A. L. Spek, J. Am. Chem. Soc., 1985, 107, 2891 [Google Scholar]
  36. C. M. Anderson, R. J. Puddephatt, G. Ferguson, A.J. Lough, J. Chem. Soc, Chem. Commun., 1989, 1297; (b) [Google Scholar]
  37. A. J. Canty, R. T. Honeyman, B. W. Skelton, A. H. White, J. Organomet. Chem., 1990, 389, 277 [Google Scholar]
  38. W. J. Pope, S. J. Peachey, Proc. Chem. Soc., London, 1907, 23, 86 [Google Scholar]
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