Synthesis and structures of nickel halide complexes bearing mono- and bis-coordinated N-heterocyclic carbene ligands, catalyzing grignard cross-coupling reactions

Organometallics

Volumn 25, Issue 14, 2006, Pages 3422-3427

  Matsubara, Kouki ^a   Ueno, Keita ^a   Shibata, Youhei ^a  

^a FUKUOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CROSSLINKING; ORGANOMETALLICS; PHOSPHORUS COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CARBENE COMPLEXES; GRIGNARD CROSS-COUPLING REACTIONS; N-HETEROCYCLIC CARBENE LIGANDS; NICKEL(II) HALIDES;

NICKEL COMPOUNDS;

EID: 33746600280     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0602658     Document Type: Article

References (49)

1. Recent reviews and textbooks for organonickel catalysis: (a) Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, 2005.
2. (b) Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995.
3. (c) Hassan, J.; Se'vignon, M.; Gozzi, C.; Schulz, E.; Lemaire M. Chem. Rev. 2002, 102, 1359-1469.
4. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
5. (e) Negishi, E. Acc. Chem. Res. 1982, 15, 340-348.
6. There are a number of reviews and books for organopalladium catalysis, for example: (a) Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: Berlin, 2005.
7. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., De Meijere, A., Eds.; Wiley: New York, 2002.
8. (c) Perspectives in Organopalladium Chemistry for the XXI Century; Tsuji, J., Ed.; Elsevier Science: Amsterdam, 1999.
9. Representative examples of nickel-complex-catalyzed cross-coupling reactions: (a) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80, and references therein.
10. (b) Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958-1969.
11. (c) Tamao, K.; Kodama, S.; Nakajima, I.; Kumada, M.; Minato, A.; Suzuki, K. Tetrahedron 1982, 38, 3347-3354.
12. (d) Negishi, E.-I.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821-1823.
13. (e) Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 37, 2993-2996.
14. (f) Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222-4223.
15. (g) Terao, J.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2003, 125, 5646-5647.
16. Coupling reactions catalyzed by nickel N-heterocyclic carbene complexes: (a) McGuinness, D. S.; Cavell, K. J. Organometallics 1999, 18, 1596-1605.
17. (b) Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Hermann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387-3389.
18. Sato, Y.; Sawaki, R.; Mori, M. Organometallics 2001, 20, 5510-5512.
19. (c) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698-3699.
20. Reviews for the carbenes: (a) Hermann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
21. (b) Weskamp, T.; Böhm V. P. W.; Herrmann W. A. J. Organomet. Chem. 2000, 600, 12-22.
22. (c) Bourissou, D.; Guerret, O.; Gabba, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
23. 2: Herrmann, W. A.; Gerstberger, G.; Spiegler, M. Organometallics 1997, 16, 2209-2212.
24. 3 palladium complexes, see: (a) Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2001, 617-618, 616-628.
25. (b) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348-352.
26. (c) Marshall, W. J.; Grushin, V. V. Organometallics 2003, 22, 1591-1593.
27. (d) Titcomb, L. R.; Caddick, S.; Cloke, F. G. N.; Wilson, D. J.; McKerrecher, D. Chem. Commun. 2001, 1388-1389.
28. (e) Frey, G. D.; Schütz, J.; Herdtweck, E.; Herrmann W. A. Organometallics 2005, 24, 4416-4426.
29. (f) Bertogg, A.; Camponovo, F.; Togni A. Eur. J. Inorg. Chem. 2005, 347-356.
30. (a) Sanford, M. S.; Love, J. A.; Grubbs R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554.
31. (b) Sanford, M. S.; Ulman, M.; Grubbs R. H. J. Am. Chem. Soc. 2001, 123, 749-750.
32. (c) Trnka, T. M.; Grubbs R. H. Acc. Chem. Res. 2001, 34, 18-29.
33. Monocarbene nickel complexes: (a) Dorta, R.; Stevens, E. D.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 10490-10491.
34. (b) Dible, B. R.; Sigman, M. S. J. Am. Chem. Soc. 2003, 125, 872-873.
35. Nickel complexes bearing two or three carbene ligands: (a) Arduengo, A. J., III; Gamper, S. F.; Calabrese, J. C.; Davidson, F. J. Am. Chem. Soc. 1994, 116, 4391-4394.
36. (b) Arnold, P. L.; Cloke, G. N.; Geldbach, T.; Hitchcock, P. B. Organometallics 1999, 18, 3228-3233.
37. (c) Douthwaite, R. E.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T. Organometallics 2001, 20, 2611-2615.
38. (d) McGuinness, D. S.; Mueller, W.; Wasserscheid, P.; Cavell, K. J.; Skelton, B. W.; White, A. H.; Englert, U. Organometallics 2002, 21, 175-181.
39. (e) Liu, Q.-X.; Xu, F.-B.; Li, Q.-S.; Song, H.-B.; Zhang, Z.-Z. Organometallics 2004, 23, 610-614.
40. (f) Clement, N. D.; Cavell, K. J.; Jones, C.; Elsevier, C. J. Angew. Chem., Int. Ed. 2004, 43, 1277-1279.
41. 2: (a) Corain, B.; Longato, B.; Angeletti, R.; Valle, G. Inorg. Chim. Acta 1985, 104, 15-18.
42. (b) Brammer, L.; Stevens, E. D. Acta Crystallogr., Sect. C 1989, 45, 400-403.
43. Grignard cross-coupling reactions using nickel catalysts: (a) Kumada, M. Pure Appl. Chem. 1980, 52, 669-679.
44. (b) Mongin, F.; Mojovic, L.; Guillamet, B.; Trecourt, F.; Queguiner, G. J. Org. Chem. 2002, 67, 8991-8994.
45. (c) Böhm, V. P. W.; Weskamp, T.; Gstöttmayr, C. W. K.; Hermann, W. A. Angew. Chem., Int. Ed. 2000, 39, 1602.
46. Krzystek, J.; Park, J.-H.; Meisel, M. W.; Hitchman, M. A.; Stratemeier, H.; Brunel, L.-C.; Telser, J. Inorg. Chem. 2002, 41, 4478-4487.
47. Venanzi, L. M. J. Chem. Soc. 1958, 719-724.
48. Arduengo,.A. J., III; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5630-5534.
49. Sheldrick, G. M. SHELXS 97 and SHELXL97-2; 1997.