Cyclometalated compounds. XVII.1 The first threefold cyclopalladation of a single benzene ring

Organometallics

Volumn 22, Issue 12, 2003, Pages 2358-2360

  Sumby, Christopher J ^a   Steel, Peter J ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOMETALATED COMPOUNDS; CYCLOPALLADATION; PALLADIUM ACETATE; PALLADIUM CHLORIDE;

AMINES; BENZENE; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; CRYSTAL STRUCTURE; PALLADIUM COMPOUNDS; X RAYS;

ORGANOMETALLICS;

EID: 0037899569     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030110p     Document Type: Article

References (61)

1. Part XVI: O'Keefe, B. J.; Steel, P. J. Organometallics 2003, 22, 1281.
2. Cope, A. C.; Siekman, R. W. J. Am. Chem. Soc. 1965, 87, 3272.
3. (a) Constable, E. C. Polyhedron 1984, 3, 1037.
4. (b) Omae, I. J. Organomet. Chem. Libr. 1986, 18, 1.
5. (c) Omae, I. Coord. Chem. Rev. 1988, 83, 137.
6. (d) Ryabov, A. D. Chem. Rev. 1990, 90, 403.
7. (e) Pfeffer, M. Recl. Trav. Chim. Pays.-Bas 1990, 109, 567.
8. Ryabov, A. D. Synthesis 1985, 233.
9. (a) Dyker, G. Chem. Ber.-Recl. 1997, 130, 1567.
10. (b) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y. S. J. Am. Chem. Soc. 1999, 121, 9531
11. (c) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917.
12. (a) Espinet, P.; Esteruelas, M. A.; Oro, L. A.; Serrano, J. L.; Sola, E. Coord. Chem. Rev. 1992, 117, 215.
13. (b) Bruce, D. W. J. Chem. Soc., Dalton Trans. 1993, 2983.
14. (c) Lydon, D. P.; Rourke, J. P. Chem. Commun. 1997, 1741.
15. (d) Cave, G. W. V.; Lydon, D. P.; Rourke, J. P. J. Organomet. Chem. 1998, 555, 81.
16. (e) Neumann, B.; Hegmann, T.; Wolf, R.; Tschierke, C. Chem. Commun. 1998, 105.
17. (f) El-Ghayourry, A.; Douce, L.; Skoulios, A.; Ziessel, R. Angew. Chem., Int. Ed. 1998, 37, 1255.
18. (g) Diez, L.; Espinet, P.; Miguel, J. A. J. Chem. Soc., Dalton Trans. 2001, 1189.
19. (a) Navarro-Ranninger, C.; Lopez-Solera, I.; Rodriguez, J.; Garcia-Ruano, J. L.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. J. Med. Chem. 1993, 36, 3795.
20. (b) Navarro-Ranninger, C.; Lopez-Solera, I.; Gonzalez, V. M.; Perez, J. M.; Alvarez-Valdes, A.; Martin, A.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. Inorg. Chem. 1996, 35, 5181.
21. (a) Izumi, T.; Kasahara, A. Bull. Yamagata Univ. Eng. 1979, 15, 213.
22. (b) Ceder, R. M.; Sales, J.; Solans, X.; Font-Altaba, M. J. Chem. Soc., Dalton Trans. 1986, 1351.
23. (c) Espinet, P.; Garcia, G.; Herrero, F. J.; Jeannin, Y.; Philoche-Levisalles, M. Inorg. Chem. 1989, 28, 4207.
24. (d) Caygill, G. B.; Hartshorn, R. M.; Steel, P. J. J. Organomet. Chem. 1990, 382, 455.
25. (e) Steel, P. J.; Caygill, G. B. J. Organomet. Chem. 1990, 395, 359.
26. (f) Jouaiti, A.; Geoffroy, M.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 3413.
27. (g) Selvakumar, K.; Vancheesan, S. Polyhedron 1996, 15, 2535.
28. (h) Vila, J. M.; Gayoso, M.; Lopez Torres, M.; Fernandez, J. J.; Fernandez, A.; Ortigueira, J. M.; Bailey, N. A.; Adams, H. J. Organomet. Chem. 1996, 511, 129.
29. (i) Lopez, C.; Bosque, R. J. Organomet. Chem. 1996, 524, 247.
30. (j) Chan, C.; Mingos, D. M. P.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 81.
31. (k) Vicente, J.; Abad, J. A.; Rink, B.; Hernández, F. S.; Ramirez de Arellano, M. C. Organometallics 1997, 16 5269.
32. (l) Wu, Y. J.; Liu, Y. H.; Yang, L.; Zhu, Q. Polyhedron 1997, 16, 335.
33. (m) de Geest, D. J.; Steel, P. J. Inorg. Chem. Commun. 1998, 1, 358.
34. Trofimenko, S. J. Am. Chem. Soc. 1971, 93, 1808.
35. (a) Chakladar, S.; Paul, P.; Venkatsubramanian, K.; Nag, K. J. Chem. Soc., Dalton Trans. 1991, 2669.
36. (b) Chakladar, S.; Paul, P.; Nag, K. Polyhedron 1991, 10, 1513.
37. (c) Chakladar, S.; Paul, P.; Mukherjee, A. K.; Dutta, S. K.; Nanda, K. K.; Podder, D.; Nag, K. J. Chem. Soc., Dalton Trans. 1992, 3119.
38. (d) Loeb, S. J.; Shimizu, G. K. J. Chem. Soc., Chem. Commun. 1993, 1395.
39. (e) Vila, J. M.; Gayoso, M.; Pereira, M. T.; Torres, M. L.; Fernandez, J. J.; Fernandez, A.; Ortigueira, J. M. J. Organomet. Chem. 1996, 506, 165.
40. (f) Steenwinkel, P.; James, S. L.; Grove, D. M.; Kooijman, H.; Spek, A. L.; van Koten, G. Organometallics 1997, 16, 513.
41. (g) Carina, R. F.; Williams, A. F.; Bernardinelli, G. J. Organomet. Chem. 1997, 548, 45.
42. (h) Hartshorn, C. M.; Steel, P. J. Organometallics 1998, 17, 3487.
43. (i) O'Keefe, B. J.; Steel, P. J. Organometallics 1998, 17, 3621.
44. (j) de Geest, D. J.; O'Keefe, B. J.; Steel, P. J. J. Organomet. Chem. 1999, 579, 97.
45. (k) Lopez-Torres, M.; Fernandez, A.; Fernandez, J. J.; Suarez, A.; Castro-Juiz, S.; Vila, J. M.; Pereira, M. T. Organometallics 2001, 20, 1350.
46. (l) Lopez-Torres, M.; Fernandez, A.; Fernandez, J. J.; Suarez, A.; Castro-Juiz, S.; Pereira, M. T.; Vila, J. M. J. Organomet. Chem. 2002, 655, 127.
47. (m) Fernandez, A.; Pereira, E.; Fernandez, J. J.; Lopez-Torres, M.; Suarez, A.; Mosteiro, R.; Pereira, M. T.; Vila, J. M. New J. Chem. 2002, 895.
48. (n) Lopez-Torres, M.; Juanatey, P.; Fernandez, J. J.; Fernandez, A.; Suarez, A.; Mosteiro, R.; Ortigueira, J. M.; Vila, J. M. Organometallics 2002, 21, 3628.
49. A tripalladated mesitylene derivative has recently been prepared by oxidative addition to triiodomesitylene, see: Vicente, J.; Lyakhovych, M.; Bautista, D.; Jones, P. G. Organometallics 2001, 20, 4695.
50. (a) van Koten, G. Pure Appl. Chem. 1989, 61, 1681.
51. (b) Rietveld, M. P. H.; Grove, D. M.; van Koten, G. New J. Chem. 1997, 21, 751.
52. (c) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759.
53. (d) Gossage, R. A.; van de Kuil, L. A.; van Koten, G. Acc. Chem. Res. 1998, 31, 423
54. (e) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 5000.
55. (f) Slagt, M. Q.; Klein Gebbink, R. J. M.; Lutz, M.; Spek, A. L.; van Koten, G. J. Chem. Soc., Dalton Trans. 2002, 2591.
56. (g) Slagt, M. Q.; Dijkstra, H. P.; McDonald, A.; Klein Gebbink, R. J. M.; Lutz, M.; Ellis, D. D.; Mills, A. M.; Spek, A. L.; van Koten, G. Organometallics 2003, 22, 27.
57. Pang, J.; Tao, Y.; Freiberg, S.; Yang, X.-P.; D'Iorio, M.; Wang, S. J. Mater. Chem. 2002, 12, 206.
58. Seward, C.; Pang, J.; Wang, S. Eur. J. Inorg. Chem. 2002, 1391.
59. 3· 2MeOH: C 42.56, H 3.01, N 11.76. Found: C 41.79, H 2.63, N 11.83.
60. It is our experience that cyclopalladated compounds frequently give combustion analyses that are low in the found carbon percentage. We believe that this is due to the formation of metal carbides in the combustion process, as has been previously noted for ruthenium complexes of similar ligands; see: Constable, E. C.; Cargill Thompson, A. W. M. J. Chem. Soc., Dalton Trans. 1992, 3467.
61. -1, GoF = 1.063, R1-[I>2σ(I)] = 0.0268, wR2(all data) = 0.0653 for 3960 reflections and 263 parameters with no restraints.