Palladium(II) and platinum(II) derivatives with N,O ligands

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Giovanni Minghetti, Sergio Stoccoro, Maria Agostina Cinellu, Antonio Zucca, Mario Manassero and Mirella Sansoni


Abstract

The preparation of a series of Pd(II) and Pt(II) derivatives with three N,O hybrid ligands 1-(2-pyridyl)ethyldiphenylphosphine oxide, L1; (2-pyridyl)methyldiphenylphosphine oxide, L2 and 2-pyridyldiphenylphosphine oxide, L3 is described. Depending on the ligand to metal molar ratio, either 1∶1 [LMCl2] {[L1PdCl2] 1, [L2PdCl2] 2, [L3PdCl2] 3, [L1PtCl2] 4} or 2∶1 [L2MCl2] {[L12PdCl2] 5, [L22PdCl2] 6, [L12PtCl2] 7} adducts are obtained. In addition, an ionic species [L12Pd][PF6]2 8, has been isolated by treatment of complex 5 with AgPF6. The structures in the solid state of compounds 5b·MeOH·H2O, 6·MeOH and 4·CH2Cl2 have been solved by X-ray diffraction. The structures of trans-[L12PdCl2] 5b (one of the diastereomers of 5) and trans-[L22PdCl2] 6 are rather different, the former being a chiral molecule (R,R enantiomer) with a C2 axis perpendicular to the plane of the metal, the latter, 6, being a centrosymmetric molecule. In both the species the ligand is bonded through the nitrogen atom. In complex [L1PtCl2] 4, the ligand is coordinated through the N and O atoms to form a six-membered ring which adopts a boat-like conformation. The structure reveals a fairly short interaction between one hydrogen atom of the Me group in an axial position and the platinum atom, Pt[hair space][hair space]· · ·[hair space][hair space]H 2.69 Å. Short contacts Pd[hair space][hair space]· · ·[hair space][hair space]H are also observed in the structures of compounds 5b and 6. Some aspects of the reactivity of the new species are discussed.


References

  1. E. Uhlig and M. Maaser, Z. Anorg. Allg. Chem., 1966, 344, 205 CrossRef CAS; C. E. Jones, B. L. Shaw and B. L. Turtle, J. Chem. Soc., Dalton Trans., 1974, 992 RSC; D. L. DuBois, W. H. Myers and D. W. Meek, J. Chem. Soc., Dalton Trans., 1975, 1011 RSC; P. Rigo, M. Bressan and M. Basato, Inorg. Chem., 1979, 18, 860 CrossRef CAS; R. Uriarte, T. J. Mazanec, K. D. Tau and D. W. Meek, Inorg. Chem., 1980, 19, 79 CrossRef; M. P. Anderson, B. M. Mattson and L. H. Pignolet, Inorg. Chem., 1983, 22, 2644 CrossRef CAS.
  2. See for example: A. Bader and E. Lindner, Coord. Chem. Rev., 1991, 108, 27 Search PubMed; J. C. JeVrey and T. B. Rauchfuss, Inorg. Chem., 1979, 18, 2658 CrossRef CAS; J. Podlahovà, B. Kratochvìl and V. Langer, Inorg. Chem., 1981, 20, 2160 CrossRef CAS; G. K. Anderson and R. Kumar, Inorg. Chem., 1984, 23, 4064 CrossRef CAS; G. P. C. M. Dekker, A. Buijs, C. J. Elsevier, K. Vrieze, P. W. N. M. van Leeuwen, W. J. J. Smeets, A. L. Spek, Y. F. Wang and C. H. Stam, Organometallics, 1992, 11, 1937 CrossRef CAS; A. Hessler, J. Fischer, S. Kucken and O. Stelzer, Chem. Ber., 1994, 127, 481 CrossRef; P. Braunstein, Y. Chauvin, J. Narhing, A. DeCian, J. Fischer, A. Tiripicchio and F. Ugozzoli, Organometallics, 1996, 15, 5551; E. Lindner, B. Keppeler, H. A. Mayer, K. Gierling, R. Fawzi and M. Steimann, J. Organomet. Chem., 1996, 526, 175 CrossRef CAS.
  3. R. W. Wegman, A. G. Abatjoglou and A. M. Harrison, J. Chem. Soc., Chem. Commun., 1987, 1891 RSC; C. Abu-Gnim and I. Amer, J. Mol. Catal., 1993, 85, L275 CrossRef CAS; E. Drent, P. Arnoldy and P. H. M. Budzelaar, J. Organomet. Chem., 1993, 455, 247 CrossRef CAS; C. Abu-Gnim and I. Amer, J. Chem. Soc., Chem. Commun., 1994, 115 RSC; C. Basoli, C. Botteghi, M. A. Cabras, G. Chelucci and M. Marchetti, J. Organomet. Chem., 1995, 488, C20 CrossRef CAS; J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter and L. Zsolnai, Tetrahedron Lett., 1994, 35, 1523 CrossRef CAS; C. G. Arena, F. Niccolò, D. Drommi and F. Faraone, J. Chem. Soc., Chem. Commun., 1994, 2251 RSC; P. Wehman, H. M. A. van Donge, A. Hagos, P. C. J. Kamer and P. W. N. M. van Leeuwen, J. Organomet. Chem., 1997, 535, 183 CrossRef CAS; G. Chelucci, M. Marchetti and B. Sechi, J. Mol. Catal. A, 1997, 122, 111 CrossRef CAS.
  4. See, for example: T. B. Rauchfuss and D. M. Roundhill, J. Am. Chem. Soc., 1974, 3098 Search PubMed; H. Brunner and A. F. M. Mokhlesur Raman, Chem. Ber., 1984, 117, 710 CrossRef CAS; D. Hedden, D. M. Roundhill, W. C. Fultz and A. L. Rheingold, J. Am. Chem. Soc., 1984, 106, 5014 CAS; M. M. Taqui Khan and A. Purshotham Reddy, Polyhedron, 1987, 6, 2009 CrossRef CAS; K. V. Baker, J. M. Brown, N. A. Cooley, G. D. Hughes and R. J. Taylor, J. Organomet. Chem., 1989, 370, 397 CrossRef CAS; S. Park, M. P. Johnson and D. M. Roundhill, Organometallics, 1989, 8, 1700 CrossRef CAS; N. W. Alcock, J. M. Brown, M. Pearson and S. Woodward, Tetrahedron: Asymmetry, 1992, 3, 17 CrossRef CAS; S. D. Perera, B. L. Shaw and M. Thornton-Pett, J. Chem. Soc., Dalton Trans., 1992, 999 CrossRef CAS; A. Albinati, F. Lianza, H. Berger, P. S. Pregosin, H. Ruegger and R. W. Kunz, Inorg. Chem., 1993, 32, 478 RSC; D. J. Law and R. G. Cavell, J. Mol. Catal., 1994, 91, 175 CrossRef CAS; S. D. Perera, B. L. Shaw and M. Thornton-Pett, J. Chem. Soc., Dalton Trans., 1994, 3311 CrossRef CAS; A. Schnyder, A. Togni and U. Wiesly, Organometallics, 1997, 16, 255 RSC; S. Chatterjee, D. C. R. Hockless, G. Salem and P. Waring, J. Chem. Soc., Dalton Trans., 1997, 3889 CrossRef CAS; P. Guillame and M. Postel, Inorg. Chem., 1997, 3889 RSC.
  5. See, for example: H. D. Empsall, P. N. Heys and B. L. Shaw, J. Chem. Soc., Dalton Trans., 1978, 257 Search PubMed; S. E. Bouaoud, P. Braunstein, D. Grandjean, D. Matt and D. Nobel, Inorg. Chem., 1986, 25, 3765 RSC; N. W. Alcock, A. W. G. Platt and P. G. Pringle, J. Chem. Soc., Dalton Trans., 1989, 139 CrossRef CAS; N. W. Alcock, A. W. G. Platt and P. G. Pringle, J. Chem. Soc., Dalton Trans., 1989, 2069 RSC; E. Lindner, J. Dettinger, H. A. Mayer, H. Kühbauch, R. Fawzi and M. Steinmann, Chem. Ber., 1993, 126, 1317 RSC; E. Lindner, Q. Wang, H. A. Mayer, R. Fawzi and M. Steinmann, Organometallics, 1993, 12, 1865 CAS; E. Lindner, J. Dettinger, R. Fawzi and M. Steinmann, Chem. Ber., 1993, 126, 1347 CrossRef CAS; E. Lindner, Q. Wang, H. A. Mayer, R. Fawzi and M. Steinmann, J. Organomet. Chem., 1993, 453, 289 CAS; E. Lindner, Q. Wang, H. A. Mayer, A. Bader, H. Kühbauch and P. Wegner, Organometallics, 1993, 12, 3291 CrossRef CAS; T. C. Blagborough, R. Davis and P. Ivison, J. Organomet. Chem., 1994, 467, 85 CrossRef CAS; P. Bhattacharyya, A. M. Z. Slawin, M. B. Smith and J. D. Woollins, Inorg. Chem., 1996, 35, 3675 CrossRef CAS; J. Andrieu, P. Braunstein, Y. Dusausoy and N. E. Germani, Inorg. Chem., 1996, 35, 7174 CrossRef CAS; E. Lindner, B. Keppeler, H. A. Mayer and K. Gierling, J. Organomet. Chem., 1996, 515, 139 CrossRef CAS.
  6. See, for example: (a) G. R. Newkome, Chem. Rev., 1993, 93, 2067 CrossRef CAS; (b) Z. Z. Zang and H. Cheng, Coord. Chem. Rev., 1996, 147, 1 CrossRef; (c) T. Suzuki, M. Kita, K. Kashiwabara and J. Fujita, Bull. Chem. Soc. Jpn., 1990, 63, 3434 CAS; (d) V. K. Jain, V. S. Jakkal and R. Bohra, J. Organomet. Chem., 1990, 389, 419 CrossRef CAS; (e) C. G. Arena, E. Rotondo, F. Faraone, M. Lanfranchi and A. Tiripicchio, Organometallics, 1991, 10, 3877 CrossRef; (f) G. De Munno, G. Bruno, C. G. Arena, D. Drommi and F. Faraone, J. Organomet. Chem., 1993, 450, 263 CrossRef; (g) C. G. Arena, G. Ciani, D. Drommi, F. Faraone, D. Proserpio and E. Rotondo, J. Organomet. Chem., 1994, 484, 71 CrossRef CAS; (h) A. Del Zotto, G. Nardin and P. Rigo, J. Chem. Soc., Dalton Trans., 1995, 3343 RSC; (i) S. Stoccoro, G. Chelucci, A. Zucca, M. A. Cinellu, G. Minghetti and M. Manassero, J. Chem. Soc., Dalton Trans., 1995, 1295 Search PubMed; (j) M. van der Sluis, V. Beverwijk, A. Termaten, E. Gavrilova, F. Bickelhaupt, H. Kooijman, N. Veldman and A. L. Spek, Organometallics, 1997, 16, 1144 CrossRef; (k) H. Yang, M. Lugan and R. Mathieu, Organometallics, 1997, 16, 2089 CrossRef CAS; (l) J. A. Casares, P. Espinet, K. Soulantica, I. Pascual and A. G. Orpen, Inorg. Chem., 1997, 36, 5251 CrossRef CAS.
  7. F. E. Wood, M. M. Olmstead, J. P. Farr and A. L. Balch, Inorg. Chim. Acta, 1985, 97, 77 CrossRef CAS.
  8. J. A. Casares, P. Espinet, J. M. Martìnez-Ilarduya and Y. S. Lin, Organometallics, 1997, 16, 770 CrossRef CAS.
  9. J.-P. Damiano, V. Munyejabo and M. Postel, Polyhedron, 1995, 14, 1229 CrossRef CAS; P. Guillame and M. Postel, Inorg. Chim. Acta, 1995, 233, 109 CrossRef.
  10. Z. Zhang, X. Wang, Z. Xi, R. Wang and H. Wang, Jiegou Huaxue, 1989, 8, 107 Search PubMed.
  11. C. Abu-Gnim and I. Amer, J. Organomet. Chem., 1996, 516, 235 CrossRef CAS.
  12. G. Minghetti, S. Stoccoro, A. Zucca, M. A. Cinellu, S. Medici and M. Manassero, III, Workshop on Platinum Chemistry, 21–24 September 1997, Gargnano, Italy, Abstract C5 Search PubMed.
  13. (a) G. R. Newkome and D. C. Hager, J. Org. Chem., 1978, 43, 947 CrossRef; (b) M. Alvarez, N. Lugan and R. Mathieu, J. Chem. Soc., Dalton Trans., 1994, 2755 RSC.
  14. F. A. Cotton, R. D. Barnes and E. Bannister, J. Chem. Soc., 1960, 2199 RSC.
  15. M. P. Anderson, C. C. Tso, B. M. Mattson and L. H. Pignolet, Inorg. Chem., 1983, 22, 3267 CrossRef CAS; K. Tani, M. Yabuta, S. Nakamura and T. Yamagota, J. Chem. Soc., Dalton Trans., 1993, 2871 RSC.
  16. S. Higgins, R. Taylor and B. L. Shaw, J. Organomet. Chem., 1987, 325, 285 CrossRef CAS; S. Gladiali, E. Alberico, S. Pulacchini and L. Kollàr, personal communication (S. Gladiali).
  17. A. Albinati, C. Arz and P. S. Pregosin, Inorg. Chem., 1987, 26, 508 CrossRef CAS; A. Albinati, P. S. Pregosin and F. Wombacher, Inorg. Chem., 1990, 29, 1812 CrossRef CAS; P. S. Pregosin and F. Wombacher, Magn. Res. Chem., 1991, 29, S106 CAS; L. Brammer, J. M. Charnock, P. L. Goggin, R. J. Goodfellow, A. G. Orpen and T. F. Koetzle, J. Chem. Soc., Dalton Trans., 1991, 1789 RSC; M. Bortolin, U. E. Bucher, H. Ruegger, L. M. Venanzi, A. Albinati, F. Lianza and S. Trofimenko, Organometallics, 1992, 11, 2514 CrossRef CAS; L. Brammer, D. Zhao, F. T. Ladipo and J. Braddock-Wilking, Acta Crystallogr., Sect. B, 1995, 51, 632 CrossRef; R. H. Crabtree, P. E. M. Siegbahn, O. Eisenstein, A. L. Rheingold and T. F. Koetzle, Acc. Chem. Res., 1996, 29, 348 CrossRef CAS; W. Yao, O. Eisenstein and R. H. Crabtree, Inorg. Chim. Acta, 1997, 254, 105 CrossRef CAS.
  18. C. K. Johnson, ORTEP, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
  19. J. E. Huheey, Inorganic Chemistry, Harper & Row, 3rd edn., 1983, p. 258 Search PubMed.
  20. (a) Comprehensive Inorganic Chemistry, Pergamon Press, 1st edn., 1973, p. 1304 Search PubMed; (b) J. A. Davies, C. M. Hockensmith, V. Y. Kukushkin and Y. N. Kukushkin, Synthetic Coordination Chemistry, Principles and Practice, World Scientific Publishing, Singapore, 1996, p. 12 Search PubMed.
  21. E. L. Eliel and S. H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1st edn., 1994 Search PubMed; C. E. Jones, B. L. Shaw and B. L. Turtle, J. Chem. Soc., Dalton Trans., 1974, 992 Search PubMed; S. Gladiali, D. Fabbri, G. Banditelli, M. Manassero and M. Sansoni, J. Organomet. Chem., 1994, 475, 307 RSC.
  22. K. Hiraki, Y. Fuchita and K. Takechi, Inorg. Chem., 1981, 20, 4316 CrossRef CAS.
  23. G. Minghetti, M. A. Cinellu, A. L. Bandini, G. Banditelli, F. Demartin and M. Manassero, J. Organomet. Chem., 1986, 315, 387 CrossRef CAS.
  24. G. R. Newkome, K. S. Theriot, F. R. Fronzek and B. Villar, Organometallics, 1989, 8, 2513 CrossRef CAS.
  25. G. Bandoli, G. Bortolozzo, D. A. Clemente, U. Croatto and C. Panattoni, J. Chem. Soc. A, 1970, 277 Search PubMed.
  26. A. C. T. North, D. C. Phillips and F. S. Mathews, Acta Crystallogr., Sect. A, 1968, 24, 351 CrossRef.
  27. (a) SAINT, Reference manual, Siemens, Energy and Automation, Madison, WI, 1994–1996; (b) G. M. Sheldrick, SADABS, Empirical Absorption Corrections Program, University of Göttingen, 1997.
  28. B. A. Frenz, Comput. Phys., 1988, 2, 42; Crystallographic Computing 5, Oxford University Press, Oxford, UK, 1991, ch. 11, p. 126 Search PubMed.
  29. International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, 1974, vol. 4 Search PubMed.
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