Synthesis, structure, and reductive elimination reactions of the first (σ-aryl)palladium complex stabilized by IPr N-heterocyclic carbene

Organometallics

Volumn 22, Issue 8, 2003, Pages 1591-1593

  Marshall, William J ^a   Grushin, Vladimir V ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC CARBENE; PHENYLIMIDAZOLIUM CATION; PHOSPHINE PREDISSOCIATION; REDUCTIVE ELIMINATION REACTIONS;

COMPLEXATION; DISSOCIATION; MOLECULAR STRUCTURE; POSITIVE IONS; REDUCTION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

PALLADIUM COMPOUNDS;

EID: 0038343553     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030099t     Document Type: Article

References (33)

1. Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913.
2. Bourissou, D.; Guerret,O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
3. Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1291.
4. For general reviews of chloroarene activation, see: Grushin, V. V.; Alper, H. Chem. Rev. 1994, 1047.
5. Grushin, V. V.; Alper, H. Top. Organomet. Chem. 1999, 3, 193.
6. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
7. For recent accounts, see: Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
8. Hillier, A. C.; Nolan, S. P. Platinum Met. Rev. 2002, 46, 50.
9. (a) Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889.
10. (b) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307.
11. (c) Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053.
12. (d) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119.
13. (e) Nolan, S. P.; Huang, J.; Trudell, M. L.; Zhang, C.; Lee, H. M. PCT Int. Appl. WO 166248 A2, 2001.
14. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
15. (g) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866.
16. (h) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229.
17. (i) Viciu, M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470.
18. 5)Pd complex has been described.
19. (b) Caddick, S.; Cloke, F. G. N.; Hitchcock, P. B.; Leonard, J.; Lewis, A. K. d. K.; McKerrecher, D.; Titcomb, L. R. Organometallis 2002, 21, 4318.
20. (c) McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596.
21. (d) Albéniz, A. C.; Espinet, P.; Manrique, R.; Pérez-Mateo, A. Angew. Chem., Int. Ed. 2002, 41, 2363.
22. 2] and [(IPr)Pd(allyl)Cl], see refs 5h and 5i, respectively.
23. 2PPd: C, 70.4; H, 6.5; N, 3.2. Found: C, 70.2; H, 6.6; N, 3.2
24. 2PPd: C, 68.4; H, 6.7; N, 3.5. Found: C, 68.0; H, 6.7; N, 3.5.
25. Flemming, J. P.; Pilon, M. C.; Borbulevitch, O. Ya.; Antipin, M. Yu.; Grushin, V. V. Inorg. Chim. Acta 1998, 280, 87.
26. int = 0.0392), SADABS correction, R1 = 0.0342 (for 12 018 reflections with I > 4σ(I)) and 0.050 (all data), wR2 = 0.0805 for 567 parameters with no restraints. The structure has been deposited with the Cambridge Crystallographic Data Center (CCDC reference number: 200331).
27. Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2001, 617-618, 616.
28. int = 0.0464), R1 = 0.0349 (for 4570 reflections with > 4σ(I)), 0.0374 (all data), wR2 = 0.0969 for 334 parameters with no restraints. The structure has been deposited with the Cambridge Crystallographic Data Center (CCDC reference number: 200332).
29. McGuinness, D. S.; Saendig, N.; Yates, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029.
30. Kong, K.-C.; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313.
31. Segelstein, B. E.; Butler, T. W.; Chenard, B. L. J. Org. Chem. 1995, 60, 12.
32. Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
33. Grushin, V. V. Organometallics 2000, 19, 1888.