Novel rhodium complexes with N-pyrrolylphosphines: attractive precursors of hydroformylation catalysts[hair space]

(Note: The full text of this document is currently only available in the PDF Version )

Anna M. Trzeciak, Tadeusz Głowiak, Ryszard Grzybek and Józef J. Ziółkowski


Abstract

New rhodium(I) complexes with N-pyrrolylphosphine ligands of formula [Rh(acac)(CO){P(NC4H4)3}] 1a, [Rh(acac)(CO){PPh(NC4H4)2}] 1b, [Rh(acac)(CO){PPh2(NC4H4)}] 1c, [Rh(acac){P(NC4H4)3}2 ] 2a, [Rh(acac){PPh(NC4H4)2} 2] 2b and [Rh(acac){PPh2(NC4H4)} 2] 2c (acac = acetylacetonate) have been found to be precursors of very active and selective hydroformylation catalysts as [RhH(CO){P(NC4H4)3}3 ] 3a, [RhH(CO){PPh(NC4H4)2}3 ] 3b and [RhH(CO){PPh2(NC4H4)}3 ] 3c respectively, which at 60 °C and 10 atm H2–CO produce 80–90% of aldehydes with n[hair space]:[hair space]iso 3–31[hair space]:[hair space]1.


References

  1. New Syntheses with Carbon Monoxide, ed. J. Falbe, Springer, Berlin, 1980 Search PubMed; I. Tkatchenko, in Comprehensive Organometallic Chemistry, ed. G. Wilkinson, Pergamon, Oxford, 1982, vol. 8, p. 101 Search PubMed; R. L. Pruett, Adv. Organomet Chem., 1979, 17, 1 Search PubMed.
  2. D. Evans, J. A. Osborn and G. Wilkinson, J. Chem. Soc. A, 1968, 3133 RSC; C. K. Brown and G. Wilkinson, J. Chem. Soc. A, 1970, 2753 RSC.
  3. C. P. Casey, G. T. Whiteker, M. G. Melville, L. M. Petrovich, J. A. Gavney, jun. and D. R. Powell, J. Am. Chem. Soc., 1992, 114, 5535 CrossRef CAS; M. Matsumoto and M. Tamura, J. Mol Catal., 1982, 16, 209 CrossRef CAS; R. Hughes and J. D. Unruh, J. Mol. Catal., 1981, 12, 71 CrossRef CAS; A. R. Sanger, Homogeneous catalysis with metal complexes, ed. L. H. Pignolet, Plenum, New York, London, 1983 Search PubMed; M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer and P. W. N. M. van Leeuwen, Organometallics, 1995, 14, 3081 Search PubMed.
  4. R. L. Pruett and J. A. Smith, J. Org. Chem., 1969, 34, 327 CrossRef CAS; R. L. Pruett, J. A. Smith and W. Va. Charleston, US Pat., 3 527 809, 1970(to Union Carbide) Search PubMed.
  5. E. Billig, A. G. Abatjoglou and D. R. Bryant, Eur. Pat. Appl., EP 214 622, 1987; US Pat., 4 769 498, 1988(to Union Carbide); and Eur. Pat. Appl., EP 213 693, 1987; US Pat., 4 748 261, 1988(to Union Carbide) Search PubMed; E. Billig, A. G. Abatjoglou, D. R. Bryant, R. E. Murray and M. J. Maher, PCT Int. Appl., WO 8 503 702, 1985; US Pat., 4 789 753, 1988(to Union Carbide) Search PubMed; M. P. Lorz, W. Bertleff, M. Roeper and D. Koeffer, Eur. Pat. Appl., EP 472 071, 1992(to BASF A.-G.) Search PubMed; P. W. N. M. van Leeuwen and G. F. Roobeek, Eur. Pat. Appl., EP 34 986, 1982, GB Appl., 80/41 098, 1980(to Shell) Search PubMed; T. J. Devon, G. W. Phillips, T. A. Puckette, J. L. Stavinoha and J. J. Vanderbilt, US Pat., 4 694 109, 1987(to Kodak) Search PubMed.
  6. H. Janecko, A. M. Trzeciak and J. J. Ziółkowski, J. Mol. Catal., 1984, 26, 355 CrossRef CAS; E. Mieczyńska, A. M. Trzeciak and J. J. Ziółkowski, J. Mol. Catal., 1992, 73, 1 CrossRef CAS; 1993, 80, 189.
  7. P. W. N. M. van Leeuwen and C. F. Roobeek, J. Organomet. Chem., 1983, 258, 343 CrossRef CAS.
  8. A. M. Trzeciak, J. J. Ziółkowski, S. Aygen and R. van Eldik, J. Mol. Catal., 1986, 34, 337 CrossRef CAS; A. M. Trzeciak, J. Organomet. Chem., 1990, 390, 105 CrossRef CAS; A. M. Trzeciak and J. J. Ziółkowski, Transition Met. Chem. (Weinheim, Ger.), 1987, 12, 408 Search PubMed.
  9. A. M. Trzeciak and J. J. Ziółkowski, J. Mol. Catal., 1987, 43, 15 CrossRef CAS.
  10. K. G. Moloy and J. L. Petersen, J. Am. Chem. Soc., 1995, 117, 7696 CrossRef.
  11. S. Fischer, J. Hoyano, I. Johnson and L. K. Peterson, Can. J. Chem., 1976, 54, 2706 CAS.
  12. R. van Eldik, S. Aygen, H. Kelm, A. M. Trzeciak and J. J. Ziółkowski, Transition Met. Chem. (Weinheim, Ger.), 1985, 10, 167 Search PubMed.
  13. A. M. Trzeciak and J. J. Ziółkowski, Inorg. Chim. Acta., 1985, 96, 15 CrossRef CAS.
  14. J. G. Leipoldt, S. S. Basson, L. D. C. Bok and T. I. A. Geber, Inorg. Chim. Acta, 1978, 26, L35 CrossRef CAS.
  15. F. Bonati and G. Wilkinson, J. Chem. Soc., 1964, 3156 RSC.
  16. J. G. Leipold, G. J. Lamprecht and E. C. Steynberg, J. Organomet. Chem., 1990, 397, 239 CrossRef.
  17. A. J. Mukhedkar, V. A. Mukhedkar, M. Green and F. G. A. Stone, J. Chem. Soc. A, 1970, 3166 RSC.
  18. E. P. Shestakova, T. G. Tcherkasova, I. S. Podkorytov and Yu. S. Varshavsky, Rhodium Express, 1994, 7–8, 17 Search PubMed.
  19. C. A. Tolman, Chem. Rev., 1977, 77, 313 CrossRef CAS.
  20. B. C. Whitmore and R. Eisenberg, J. Am. Chem. Soc., 1984, 106, 3225 CrossRef CAS.
  21. J. G. Leipoldt, G. J. Lamprecht and G. J. van Zyl, Inorg. Chim. Acta, 1985, 96, L31 CrossRef CAS.
  22. J. G. Leipold, S. S. Basson and C. R. Dennis, Inorg. Chim. Acta, 1981, 50, 121 CrossRef.
  23. J. G. Leipold, L. D. C. Bok, S. S. Basson and H. Meyer, Inorg. Chim. Acta, 1980, 42, 105 CrossRef.
  24. J. L. Atwood, A. H. Cowley, W. E. Hunter and S. K. Mehrotra, Inorg. Chem., 1982, 21, 1354 CrossRef CAS.
  25. F. H. Jardine and P. S. Sheridan, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, Pergamon, Oxford, 1987 Search PubMed.
  26. S. J. La Placa and J. J. Ibers, Acta Crystallogr., 1965, 18, 511 CrossRef CAS.
  27. A. M. Trzeciak and J. J. Ziółkowski, J. Mol. Catal., 1986, 34, 213 CrossRef CAS.
  28. Yu. S. Varshavsky and T. G. Tcherkasova, Zh. Neorg. Khim, 1967, 12, 1709 Search PubMed.
  29. R. Cramer, Inorg. Synth., 1976, 15, 14.
  30. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467 CrossRef.
  31. G. M. Sheldrick, SHELXL 93, Program for the Refinement of Crystal Structures, University of Göttingen, 1994.
Click here to see how this site uses Cookies. View our privacy policy here.