Stable palladium(0), palladium(II), and platinum(II) complexes containing a new, multifunctional and hemilabile phosphino-imino-pyridyl ligand: Synthesis, characterization, and reactivity

Organometallics

Volumn 15, Issue 13, 1996, Pages 3022-3031

  Rülke, Richard E ^a   Kaasjager, Vincent E ^a   Wehman, Petra ^a   Elsevier, Cornelis J ^a   Van Leeuwen, Piet W N M ^a   Vrieze, Kees ^a   Fraanje, Jan ^a   Goubitz, Kees ^a   Spek, Anthony L ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037852389     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9509047     Document Type: Article

References (73)

1. (a) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Elsevier, C. J. J. Chem. Soc., Chem. Commun. 1993, 1203.
2. (b) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977.
3. (c) Dekker, G. P. C. M.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K. J. Organomet. Chem. 1992, 430, 357.
4. (d) Tóth, I.; Elsevier, C. J. J. Am. Chem. Soc. 1993, 115, 10388.
5. (e) Rülke, R. E.; Kliphuis, D.; Elsevier, C. J.; Fraanje, J.; Goubitz, K.; van Leeuwen, P. W. N. M.; Vrieze, K. J. Chem. Soc., Chem. Commun. 1994, 1817.
6. (a) van Asselt, R.; Elsevier, C. J. Organometallics 1992,11, 1999.
7. (b) van Asselt, R.; Elsevier, C. J. Tetrahedron 1994, 50, 323.
8. (c) Wehman, P.; Dol, G. C.; Moorman, E. R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Fraanje, J.; Goubitz, K. Organometallics 1994, 13, 4856.
9. (d) Wehman, P.; Kaasjager, V. E.; de Lange, W. G. J.; Hartl, F.; Kamer, P. C. J.; van Leeuwen, P. W, N. M.; Fraanje, J.; Goubitz, K. Organometallics 1995, 14, 3751.
10. (e) Wehman, P.; Borst, L.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1996, 217.
11. (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron Asymm. 1992, 3, 1089.
12. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3435.
13. (a) Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180.
14. (b) Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395.
15. (c) Hayashi, T.; Hagihara, T.; Katsuro, Y.; Kumada, M. Bull. Chem. Soc. Jpn. 1983, 56, 363.
16. (d) Hayashi, T.; Ito, Y.; Yamamoto, A. J. Chem. Soc., Chem. Commun. 1986, 1090.
17. (e) Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191.
18. (f) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
19. (g) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
20. (h) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
21. (i) von Matt, P.; Loiseleur, O.; Koch, G.; Pfaltz, A.; Lefeber, C.; Feucht, T.; Helmchen, G. Tetrahedron Asymm. 1994, 5, 573.
22. (j) Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595.
23. (k) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523.
24. (l) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493.
25. (m) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1995, 36, 461.
26. (a) Jedlicka, B.; Kratky, C.; Weissensteiner, W.; Widhalm, M. J. Chem. Soc., Chem. Commun. 1993, 1329.
27. (b) Jedlicka, B.; Weissensteiner, W.; Zsolnai, L.; Huttner, G. Organometallics, in preparation.
28. (c) Jedlicka, B.; Rülke, R. E.; Weissensteiner, W.; Galán, R. F.; Jalón, F. A.; Manzano, B. M.; Robriguez-de la Fuente, J.; Veldman, N.; Spek, A. L. J. Organomet. Chem., in press.
29. (d) Jedlicka, B.; Weissensteiner, W.; Veldman, N.; Spek, A. L.; Vrieze, K. Organometallics, submitted for publication.
30. Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron Asymm. 1994, 5, 1895. Other S-N ligands are reported in ref 4k.
31. Wehman, P.; Rülke, R. E.; Kaasjager, V. E.; Elsevier, C. J.; Kooijman, H.; Spek, A. L.; Vrieze, K.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1995, 331.
32. (a) Rauchfuss, T. B. J. Organomet. Chem. 1978, 162, C19.
33. (b) Jeffery, J. C.; Rauchfuss, T. B.; Tucker, P. A. Inorg. Chem. 1980, 19, 3306.
34. Lavery, A.; Nelson, S. M. J. Chem. Soc., Dalton Trans. 1984, 615.
35. See for example: (a) Contreras, R. H.; Facelli, J. C. In Annual Reports in NMR Spectroscopy; Webb, G. A., Ed.; Academic Press Ltd.: London, England, 1993. (b) Jameson, C. J. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis;. Verkade, J. G., Quin, L. D., Eds.; VHC: Deerfield Beach, FL, 1987.
36. See for example: (a) Contreras, R. H.; Facelli, J. C. In Annual Reports in NMR Spectroscopy; Webb, G. A., Ed.; Academic Press Ltd.: London, England, 1993. (b) Jameson, C. J. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis;. Verkade, J. G., Quin, L. D., Eds.; VHC: Deerfield Beach, FL, 1987.
37. Rülke, R. E.; Ernsting, J. M.; Spek, A. L.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K. Inorg. Chem. 1993, 32, 5769.
38. (a) Buchanan, G. W. Tetrahedron 1985, 45, 581.
39. (b) von Philipsborn, W.; Müler, R. Angew. Chem., Int. Ed. Engl. 1986, 25, 383.
40. (c) Pregosin, P. S.; Ruedi, R.; Anklin, C. Magn. Reson. Chem. 1986, 24, 255.
41. Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y.-F.; Stam, C. H. Organometallics 1992, 11, 1937.
42. Rülke, R. E.; Kaasjager, V. E.; Kliphuis, D.; Elsevier, C. J.; Goubitz, K.; van Leeuwen, P. W. N. M.; Vrieze, K. Organometallics 1996, 15, 668.
43. (a) Sacco, A.; Vasopollo, G.; Nobile, C. F.; Piergiovanni, A.; Pellinghelli, M.; A.; Lanfranchi, M. J. Organomet. Chem. 1988, 356, 397 (with Pd-P = 2.290(3) Å, Pd-N = 2.073(8) Å, Pd-C = 1.991(10) A, and P-Pd-N = 83.6(2)° (five-membered ring)).
44. (b) Cecconi, F.; Ghilardi, C. A.; Midollini, S.; Monetti, S.; Orlandini, A.; Scapacci, G. J. Chem. Soc., Dalton Trans. 1989,211 (with Pd-P = 2.357(4) Å, Pd-N = 2.23(2) Å, and P-Pd-N = 84.6(1)° (five-membered ring)).
45. (c) Clark, G. R.; Palenik, G. J. Inorg. Chem. 1970, 9, 274 (with Pd-P = 2.243 Å, Pd-N = 2.148 Å, and P-Pd-N = 92.4° (six-membered ring)).
46. (a) Roe, D. C. J. Magn. Reson. 1985, 63, 388.
47. (b) For applications in palladium chemistry, see: Elsevier, C. J. J. Mol. Catal. 1994, 92, 285.
48. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
49. Rülke, R. E.; Delis, J. G. P.; Groot, A. M.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K.; Schenk, H. J. Organomet. Chem. 1996, 508, 109.
50. (a) Bardi, R.; del Pra, A.; Piazzesi, A. M.; Toniolo, L. Inorg. Chim. Acta 1979, 35, L345.
51. (b) Bardi, R.; Piazzesi, A. M.; Cavinato, G.; Cavoli, P.; Toniolo, L. J. Organomet. Chem. 1982, 224, 407.
52. (c) Bardi, R.; Piazzesi, A. M.; del Pra, A.; Cavinato, G.; Toniolo, L. Inorg. Chim. Acta 1985, 102, 99.
53. (d) Markies, B. A.; Wijkens, P.; Boersma, J.; Spek, A. L.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1991, 110, 133.
54. Dent, W. T.; Long, R.; Wilkinson, A. J. J. Chem. Soc. 1964, 1585.
55. Numata, S.; Okawara, R.; Kurosawa, H. Inorg. Chem. 1977, 16, 1737.
56. (a) Cotton, F. A.; Faller, J. W.; Musco, A. Inorg. Chem. 1967, 6, 179.
57. (b) Powell, J.; Shaw, B. L. J. Chem. Soc. A 1967, 1839.
58. (c) Kurosawa, H.; Kajimaru, H.; Ogoshi, S.; Yoneda, H.; Miki, K.; Kasai, N.; Murai, S.; Ikeda, I. J. Am. Chem. Soc. 1992, 114, 8417.
59. Ankersmit, H. A.; Veldman, N.; Spek, A. L.; Eriksen, K.; Goubitz, K.; Vrieze, K.; van Koten, G. Inorg. Chim. Acta, in press.
60. Åkermark, B.; Krakenberger, B.; Hansson, S.; Vitagliano, A. Organometallics 1987, 6, 620.
61. Rülke, R. E.; Han, I. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F.; Zoutberg, M. Stam, C. H. Inorg. Chim. Acta 1990, 169, 5.
62. (a) Yoshida, G.; Numata, S.; Kurosawa, H. Chem. Lett. 1976, 705.
63. (b) Kurosawa, H.; Yoshida, G. J. Organomet. Chem. 1976, 120, 297.
64. 15N-INEPT-NMR spectroscopy, see: Benn, R.; Günther, H. Angew. Chem. 1983, 95, 381.
65. Rauchfuss, T. B.; Wrobleski, D. A. Inorg. Synth. 1982, 21, 175.
66. Walker, N.; Stuart, D. Acta Crystallogr., Sect. A 1983, 39, 158.
67. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. D.; Smits, J. M. M.; Smykalla, C. The DIRDIF program system; Technical report of the Crystallographic Laboratory, Universiteit Nijmegen: Nijmegen, The Netherlands, 1992.
68. Sheldrick, G. M. SHELX-76, Crystal Structure Analysis Package; University of Cambridge: Cambridge, England, 1976.
69. (a) Cromer, D. T.; Mann, J. B. Acta Crystallogr., Sect. A 1968, 24, 321.
70. (b) Cromer, D. T.; Liberman, D. J. Chem. Phys. 1970, 53, 1891.
71. Spek, A. L. Acta Crystallogr., Sect. A 1990, 46, C34.
72. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1975; Vol. 4.
73. XTAL 3.2 Reference Manual; Hall, S. R., Stewart, J. M., Eds.; Universitites of Western Australia, Perth, Australia, and of Maryland, College Park, MD, 1992.