Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene)

Organometallics

Volumn 23, Issue 7, 2004, Pages 1629-1635

  Viciu, Mihai S ^a   Navarro, Oscar ^a   Germaneau, Romain F ^a,c   Kelly III, Roy A ^a   Sommer, William ^a   Marion, Nicolas ^a,c   Stevens, Erwin D ^a   Cavallo, Luigi ^b   Nolan, Steven P ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b UNIVERSITY OF SALERNO   (Italy)

^c SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPLEXATION; CRYSTAL STRUCTURE; PALLADIUM COMPOUNDS; PERTURBATION TECHNIQUES; REACTION KINETICS; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ARYL AMINATION; HETEROCYCLIC CARBENE; LIGAND STERIC PROPERTIES;

ORGANOMETALLICS;

EID: 1842740885     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034319e     Document Type: Article

References (42)

1. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
2. (b) Hillier, A. C.; Nolan, S. P. Platinum Met. Rev. 2002, 46, 50-64.
3. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
4. (a) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
5. (b) Viciu, M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470-5472.
6. DiRenzo, G. M.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 6225-6234.
7. For a similar protocol see: Arduengo, A. J. III; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
8. (a) Ramey, K. C.; Statton, G. L. J. Am. Chem. Soc. 1966, 88, 4387-4390.
9. (b) Powell, J.; Shaw, B. L. J. Chem. Soc. A 1967, 11, 1839-1851.
10. (c) Mann, B. E.; Pietropaolo, R.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1973, 22, 2390-2393.
11. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
12. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
13. (b) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423-1426.
14. Hillier, A. C.; Sommer, W. J.; Yong, B. S.; Petersen, J. L.; Cavallo, L.; Nolan, S. P. Organometallics 2003, 22, 4322-4326.
15. (a) Herrmann, W. A.; Elison, M.; Fischer, J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371-2374.
16. (b) McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596-1605.
17. Arduengo, A. J., III; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028.
18. (a) See discussion on steric control for bulky phosphines: Galardon, E.; Ramedeehul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem., Int. Ed. 2002, 41, 1760-1763, and references cited.
19. (b) For a recent example of associative mechanism for oxidative addition in palladium systems see: Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5749-5752.
20. (a) Galardon, E.; Ramdeehul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem., Int. Ed. 2002, 41, 1760-1763.
21. (b) McGuiness, D.; Cavell, K. J. Organometallics Organometallics 2000, 19, 741-748.
22. (c) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1987; p 322.
23. (a) Marshall, W. J.; Grushin, V. V.; Organometallics 2003, 22, 1591-1593.
24. (b) McGuinness, D. S.; Green, M. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1998, 565, 165-178.
25. (c) McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 4918-4920.
26. (d) McGuinness, D. S.; Saendig, N.; Yates, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029-4040.
27. Grushin, V. V. Organometallics 2000, 19, 1888-1900.
28. Titcomb, L. R.; Caddick, S.; Cloke, F. G. N.; Wilson, D. J.; McKerrecher, D. Chem. Commun. 2001, 1388-1389.
29. (a) Caddick, S.; Cloke, F. G. N.; Hitchcock, P. B.; Leonard, J.; de Lewis, A. K.; McKerrecher, D.; Titcomb, L. R. Organometallics 2002, 21, 4318-4319.
30. (b) De Lewis, A. K.; Caddick, S.; Cloke, F. G. N.; Billingham, N. C.; Hitchcock, P. B.; Leonard, J. Am. Chem. Soc. 2003, 123, 10066-10073.
31. Reductive elimination of electron-rich N-heterocycle from Pd(II)/phosphine centers has been discussed in detail: (a) Hartwig, J. F. Acc. Chem. Res. 1998, 21, 852-860.
32. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827-828.
33. (c) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
34. (d) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729-7737, It is assumed to be slow, but it is accelerated for low ratio phosphines/palladium (T or Y configuration for 1:1 ratio) or chelating bis-phosphines that force product elimination.
35. Dorta, R.; Stevens, D. S.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 10490-10491.
36. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd ed.; John Wiley & Sons; New York, 2001.
37. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
38. Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921.
39. N1, N3 denote the nitrogens and C4, C5 the backbone carbon atoms of imidazole (dihydroimidazole ring). The torsion angles were calculated from crystallographic data.
40. (CHMe2) bond distances in 1 are 3.710, 3.543, 4.902, and 4.956 Å. As observed, the ligand environment around the metal center is substantially different.
41. Tsuji, Y.; Huh, K. T.; Ohsugi, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1365-1370.
42. The synthesis of the NHC from the corresponding imidazolium salts is adapted from a previously reported protocol: see ref 6.