Divalent palladium and platinum complexes containing rigid bidentate nitrogen ligands and electrochemistry of the palladium complexes

Organometallics

Volumn 16, Issue 3, 1997, Pages 317-328

  Van Asselt, Rob ^a   Elsevier, Cornelis J ^a   Amatore, Christian ^b   Jutand, Anny ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000303183     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960578a     Document Type: Article

References (71)

1. Rigid Bidentate Nitrogen Ligands in Organometallic Chemistry and Homogeneous Catalysis. 11. Part 9: Reference 9. Part 10: van Belzen, R.; Klein, R. A.; Smeets, W. J. J.; Spek, A. L.; Benedix, R.; Elsevier, C. J. Recl. Trav. Chim. Pays-Bas 1996, 115, 275.
2. (a) Leconte, P.; Metz, F.; Mortreux, A.; Osborn, J. A.; Paul, F.; Petit, F.; Pillot, A. J. Chem. Soc., Chem. Commun. 1990, 1616.
3. (b) Ugo, R.; Psaro, R.; Pizzotti, M.; Nardi, P.; Dossi, C.; Andreetta, A.; Capparella, G. J. Organomet. Chem. 1991, 417, 211.
4. (c) Drent, E. Pure Appl. Chem. 1990, 62, 661.
5. (a) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
6. (b) Kumada, M. Pure Appl. Chem. 1980, 52, 669.
7. (c) Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 75, 395.
8. (d) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749.
9. (e) Honeychuck, R. V.; Okoroafor, M. O.; Shen, L. H.; Brubaker, C. H., Jr. Organometallics 1986, 5, 482.
10. (f) Yamamoto, A. Organotransition Metal Chemistry; Wiley: New York, 1986; pp 374-399.
11. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138.
12. (h) Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393.
13. (i) Ali, H. M.; Brubaker, C. H., Jr. J. Mol. Catal. 1990, 60, 331.
14. (j) Wright, M. E.; Lowe-Ma, C. K. Organometallics 1990, 9, 347.
15. (k) Hatanaka, Y.; Hiyama, T. Synlett. 1991, 845.
16. Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
17. Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
18. (a) Baker, K. V.; Brown, J. M.; Cooley, N. A.; Hughes, G. D.; Taylor, R. J. J. Organomet. Chem. 1990, 370, 397.
19. (b) Brown, J. M.; Cooley, N. A. Organometallics 1990, 9, 353.
20. Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
21. (a) van Asselt, R.; Elsevier, C. J. Organometallics 1992, 12, 1999.
22. (b) van Asselt, R.; Elsevier, C. J. Tetrahedron 1994, 50, 323.
23. (c) van Asselt, R.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977.
24. van Asselt, R.; Vrieze, K.; Elsevier, C. J. J. Organomet. Chem. 1994, 480, 27.
25. (a) Negishi, E.; Takahashi, T.; Akiyoshi, K. J. Chem. Soc., Chem. Commun. 1986, 1338.
26. (b) Urata, H.; Suzuki, H.; Moro-oka, Y.; Ikawa, T. J. Organomet. Chem. 1989, 364, 235.
27. Mason, M. R.; Verkade, J. G. Organometallics 1992, 11, 2212.
28. (a) Paonessa, R. S.; Prignano, A. L.; Trogler, W. C. Organometallics 1985, 4, 647.
29. (b) Trogler, W. C. In Excited States and Reactive Intermediates: ACS Symposium Series 307, Lever, A. B. P., Ed.; American Chemical Society: Washington, DC, 1986; pp 188-191.
30. Knoll, H.; Stich, R.; Hennig, H.; Stufkens, D. J. Inorg. Chim. Acta 1990, 178, 11.
31. (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Organomet. Chem. 1989, 363, C41.
32. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670.
33. (c) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375.
34. (d) Amatore, C.; Jutand, A.; Khalil, A. F.; Nielsen, M. F. J. Am. Chem. Soc. 1992, 114, 7076.
35. (a) Paumard, E.; Mortreux, A.; Petit, F. J. Chem. Soc., Chem. Commun. 1989, 1380.
36. (b) Davies, J. A.; Staples, R. J. Polyhedron 1991, 10, 909.
37. Kharasch, M. S.; Seyler, R. C.; Mayo, F. R. J. Am. Chem. Soc. 1938, 60, 882.
38. Kaufmann, G. B.; Cowan, D. O. Inorg. Synth. 1960, 6, 211.
39. Chock, P. B.; Halpern, J.; Paulik, F. E. Inorg. Synth. 1973, 14, 90.
40. (a) Matei, I.; Lixandru, T. Bul. Inst. Politeh. Iasi 1967, 13, 245; Chem. Abstr. 1969, 70, 3623.
41. (a) Matei, I.; Lixandru, T. Bul. Inst. Politeh. Iasi 1967, 13, 245; Chem. Abstr. 1969, 70, 3623.
42. (b) Normant, M. H. C. R. Seances Acad. Sci., Ser. C 1969, 268, 1811.
43. (c) van Asselt, R.; Elsevier, C. J.; Smeets, W. J. J.; Spek, A. L. Benedix, R. Recl. Trav. Chim. Pays-Bas 1994, 113, 88.
44. Amatore, C.; Lefrou, C.; Pflüger, F. J. Electroanal. Chem. Interfacial Electrochem. 1989, 270, 43.
45. Amatore, C.; Azzabi, M.; Calas, P.; Jutand, A.; Lefrou, C.; Rollin, Y. J. Electroanal. Chem. Interfacial Electrochem. 1990, 288, 45.
46. Maresca, L.; Natile, G.; Cattalini, L. Inorg. Chim. Acta 1975, 14, 79.
47. (a) Palocsay, F. A.; Rund, J. V. Inorg. Chem. 1969, 8, 524.
48. (b) Rund, J. V.; Palocsay, F. A. Inorg. Chem. 1969, 8, 2242.
49. Fanizzi, F. P.; Intini, F. P.; Maresca, L. J. Chem. Soc., Dalton Trans. 1990, 199.
50. van Asselt, R.; Elsevier, C. J.; Smeets, W. J. J.; Spek, A. L. Inorg. Chem. 1994, 33, 1521.
51. (a) van der Poel, H.; van Koten, G.; Vrieze, K. Inorg. Chem. 1980, 19, 1145.
52. (b) Navarro-Ranninger, M. C.; Camazon, M. J.; Alvarez-Valdes, A.; Masaguer, J. R.; Martinez-Carrera, S.; Garcia-Blanco, S. Polyhedron 1987, 6, 1059.
53. (c) Crociani, B.; Di Bianca, F.; Bertani, R.; Zanotto, L. Inorg. Chim. Acta 1988, 141, 253.
54. (d) Zaghal, M. H.; Qaseer, H. A. Transition Met. Chem. 1991, 16, 39.
55. Chaudhury, N.; Puddephatt, R. J. J. Organomet.Chem. 1975, 84, 105.
56. 4NCl (5-60 equiv relative to the palladium complex) was added to the solution.
57. 0′ For an example of reversible dimerization, see: Smith, C. R.; Utley, J. H. P.; J. Chem. Res., Synop. 1982, 18.
58. .- cannot be involved in the equilibrium reported above in ref 29a.
59. (a) Braterman, P. S.; Song, J. I.; Vogler, C.; Kaim, W. Inorg. Chem. 1992, 31, 222.
60. (b) Braterman, P. S.; Song, J. I.; Wimmer, F. M.; Wimmer, S.; Kaim, W.; Klein, A.; Peacock, R. D. Inorg. Chem. 1992, 31, 5084.
61. (c) Vogler, C.; Schwederski, B.; Klein, A.; Kaim, W. J. Organomet. Chem. 1992, 436, 367.
62. (d) Klein, A.; Hausen, H. D.; Kaim, W. J. Organomet. Chem. 1992, 440, 207.
63. (a) Martin, M.; Krogh-Jespersen, M. B.; Hsu, M.; Tewksbury, J.; Laurent, M.; Viswanath, K.; Patterson, H. Inorg. Chem. 1983, 22, 647.
64. (b) Kamath, S. S.; Uma, V.; Srivastava, T. S. Inorg. Chim. Acta 1989, 161, 49.
65. 14
66. Ito, N.; Saji, T. Aoyagui, S. Bull. Chem. Soc. Jpn. 1985, 58, 2323.
67. The reduction peak potentials (in THF) of the alkenes employed in this work are (corresponding oxidation peak potentials in parentheses): MA, -0.82 V (irr); DMFU, -1.44 V (-1.30 V); DMM, -1.55 V (-1.41 V); MeAC, -2.21 V (irr).
68. 14c
69. In view of some current studies involving Ar-BIAN and similar rigid ligands we cannot, however, exclude the possibility that one nitrogen of the Ar-BIAN dissociates, followed by addition of another Ar′-BIAN molecule, generating as an intermediate a Pd(Ar-BIAN)(Ar′-BIAN)(alkene) complex in which two BIAN ligands are (monodentate) coordinated.
70. 15b
71. van Asselt, R.; Elsevier, C. J. J. Mol. Catal. 1991, 65, L13.