A comparative study of the chelating ability of the -N(R)-(CH 2)n-CO-N(R)2 framework in σ-aryl palladium(II) complexes derived from 2-iodoanilines and 2-iodobenzylamines. Synthesis of new types of terdentate [C,N,O] Pd(II) complexes and C,N-bridged binuclear Pd(II) compounds

Organometallics

Volumn 25, Issue 8, 2006, Pages 1995-2001

  Solé, Daniel ^a   Díaz, Sandra ^a   Solans, Xavier ^a   Font Bardia, Mercè ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHELATION; PALLADIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BINUCLEAR PD(II) COMPLEXES; PALLADIUM COMPLEXES; TERDENTATE [C,N,O] PD(II) COMPLEXES;

ORGANOMETALLICS;

EID: 33646343189     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om051014m     Document Type: Article

References (37)

1. For recent reviews, see: (a) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917-1927.
2. (b) Bedford, R. B. Chem. Commun. 2003, 1787-1796.
3. (c) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527-2572.
4. Vila, J. M.; Pereira, M. T.; Suárez, A.; Fernández, J. J.; Ortigueira, J. M.; Fernández, A.; Torres, M. L.; Rodríguez, C. Trends Organomet. Chem. 1999, 3, 71-98.
5. [C,N,O] acetylhydrazone- and semicarbazone-derived complexes: (a) Nonoyama, M.; Sugimoto, M. Inorg. Chim. Acta 1979, 35, 131-134.
6. (b) Sugimoto, M.; Nonoyama, M. Inorg. Nucl. Chem. Lett. 1979, 15, 405-408.
7. (c) Nonoyama, M. J..Inorg. Nucl. Chem. 1980, 42, 297-299.
8. (d) Nonoyama, M. Inorg. Chim. Acta 1988, 145, 53-56.
9. (e) Tollari, S.; Palmisano, G.; Demartin, F.; Grassi, M.; Magnaghi, S.; Cenini, S. J. Organomet. Chem. 1995, 488, 79-83.
10. (f) Vila, J. M.; Pereira, T.; Ortigueira, J. M.; Torres, M. L.; Castiñeiras, A.; Lata, D.; Fernández, J. J.; Fernández, A. J. Organomet. Chem. 1998, 556, 21-30.
11. (g) Fernández, A.; López-Torres, M.; Suárez, A.; Ortigueira, J. M.; Pereira, T.; Fernández, J. J.; Vila, J. M.; Adams, H. J. Organomet. Chem. 2000, 598, 1-12.
12. [C,N,O] benzoylhydrazone-derived complexes: Das, S.; Pal, S. J. Organomet. Chem. 2004, 689, 352-360.
13. [C,N,O] phenylhydrazone-derived complexes: (a) Albert, J.; González, A.; Granell, J.; Moragas, R.; Puerta, C.; Valerga, P. Organometallics 1997, 16, 3775-3778.
14. (b) Albert, J.; González, A.; Granell, J.; Moragas, R.; Solans, X.; Font-Bardia, M. J. Chem. Soc., Dalton Trans. 1998, 1781-1785.
15. [C,N,O] imine-derived complexes: (a) Yang, H.; Khan, M. A.; Nicholas, K. M. J. Chem. Soc., Chem. Commun. 1992, 210-212.
16. (b) Zhao, G.; Wang, Q.-G.; Mak, T. C. W. Organometallics 1998, 17, 3437-3441.
17. (c) Zhao, G.; Wang, Q.-G.; Mak, T. C. W. J. Chem. Soc., Dalton Trans. 1998, 3785-3789.
18. (d) Zhao, G.; Wang, Q.-G.; Mak, T. C. W. J. Organomet. Chem. 1999, 574, 311-317.
19. (e) Cativiela, C.; Falvello, L. R.; Ginés, J. C.; Navarro, R.; Urriolabeitia, E. P. New J. Chem. 2001, 25, 344-352.
20. (f) Fernández, A.; Pereira, E.; Fernández, J. J.; López-Torres, M.; Suárez, A.; Mosteiro, R.; Vila, J. M. Polyhedron 2002, 21, 39-48.
21. (g) Fernández, A.; Vázquez-García, D.; Fernández, J. J.; López-Torres, M.; Suárez, A.; Castro-Juiz, S.; Vila, J. M. New J. Chem. 2002, 26, 398-404.
22. [C,N,O] 8-hydroxyquinoline-derived complexes: Yoneda, A.; Hakushi, T.; Newkome, G. R.; Froncsek, F. R. Organometallics 1994, 13, 4912-4918, and references therein.
23. [C,N,O] diarylazo complexes: Steiner, E.; L'Eplattenier, F. A. Helv. Chim. Acta 1978, 61, 2264-2268.
24. (a) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587-1594.
25. (b) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. Organometallics 2004, 23, 1438-1447.
26. Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardia, M. Chem. Commun. 2005, 2738-2740.
27. For an example of the acetamido group in which the N competes with the O coordination for the Pd atom depending on the size of the cyclometalated ring, see: Dupont, J:; Pfeffer, M.; Daran, J. C.; Gouteron, J. J. Chem. Soc., Dalton Trans. 1988, 2421-2429.
28. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
29. For the preparation of Pd(II) complexes with coordination by one of the carbonyl groups of the phthaloyl moiety, see: Enzmann, A.; Eckert, M.; Ponikwar, W.; Polborn, K.; Schneiderbauer, S.; Beller, M.; Beck, W. Eur. J. Inorg. Chem. 2004, 1330-1340.
30. 9a
31. However, it should be noted that the generation of a transient [C,N,O] terdentate [4,5] Pd(II) complex, which then would evolve to the more stable binuclear Pd(II) complex, could not be completely rejected.
32. 1H NMR spectra of 11a and 11b showed broad signals. If one proton is assigned to the resonance with the least integration in the spectra of 11a and 11b, 46 and 38 protons are obtained, respectively, which corresponds at least to a dimeric structure for these complexes (see Experimental Section).
33. For an example in which the simultaneous coordination of sulfur and oxygen atoms in a multidonor ligand results in the formation of polymeric species, see: Vicente, J.; Chicote, M.-T.; Rubio, C.; Ramírez de Arellano, M. C.; Jones, P. G. Organometallics 1999, 18, 2750-2759.
34. -1 less favorable than the corresponding five-membered counterpart. Bosque, R.; Maseras, F. Eur. J. Inorg. Chem. 2005, 4040-4047.
35. (a) Singhal, A.; Jain, V. K.; Nethaji, M.; Samuelson, A. G.; Jayaprakash, D.; Butcher, R. J. Polyhedron 1998, 17, 3531-3540.
36. (b) Dupont, J.; Pfeffer, M.; Daran, J. C.; Jeannin, Y. Organometallics 1987, 6, 899-901, and references therein.
37. Sheldrick, G. M. SHELXL97, computer program for the determination of crystal structure; University of Göttingen: Germany, 1997.