An unsaturated nickel(0) NHC catalyst: Facile preparation and structure of Ni(0)(NHC)2, featuring a reduction process from Ni(II)(NHC)(acac) 2

Organometallics

Volumn 27, Issue 22, 2008, Pages 6020-6024

  Matsubara, Kouki ^a   Miyazaki, Satoshi ^a   Koga, Yuji ^a   Nibu, Yoshinori ^a   Hashimura, Takaaki ^a   Matsumoto, Taisuke ^b  

^a FUKUOKA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL;

CARBENE; FACILE PREPARATIONS; NHC LIGANDS; NI(ACAC)2; REDUCTION PROCESSES; SYNTHETIC ROUTES; UNSATURATED STRUCTURES;

NICKEL ALLOYS;

EID: 57049100929     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800488x     Document Type: Article

References (48)

1. (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.; Sévignon, 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. Ace Chem. Res. 1982, 15, 340-348.
6. (a) N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, 2006.
7. (b) Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247-2273.
8. (c) Scott, N. M.; Nolan, S. P. Eur. J. Inorg. Chem. 2005, 1815-1828.
9. (d) Herrmann, W. A.; Schütz, J.; Frey, G. D.; Herdtweck, E. Organometallics 2006, 25, 2437-2448.
10. (e) Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883.
11. (f) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122-3172.
12. (g) Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768-2813.
13. (a) Matsubara, K.; Ueno, K.; Shibata, Y. Organometallics 2006, 25, 3422-3427.
14. (b) Matsubara, K.; Ueno, K.; Koga, Y.; Hara, K. J. Org. Chem. 2007, 72, 5069-5076.
15. (a) Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387-3389.
16. (b) Sato, Y.; Sawaki, R.; Mori, M. Organometallics 2001, 20, 5510-5512.
17. (c) Normand, A. T.; Hawkes, K. J.; Clement, N. D.; Cavell, K. J.; Yates, B. F. Organometallics 2007, 26, 5352-5363.
18. (d) Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964-15965.
19. (e) Schaub, T.; Backes, M.; Radius, U. Organometallics 2006, 25, 4196-4206.
20. (a) Aresta, A.; Nobile, C. F.; Sacco, A. Inorg. Chim. Acta 1975, 12, 167-178.
21. (b) Morvillo, A.; Turco, A. J. Organomet. Chem. 1982, 224, 387-397.
22. (c) Jonas, K. J. Organomet. Chem. 1974, 78, 273-279.
23. Danopoulos, A. A.; Pugh, D. Dalton Trans. 2008, 30-31.
24. Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2003, 22, 4184-4186, and references therein.
25. Navarro, O.; Marion, N.; Scott, N. M.; González, J.; Amoroso, D.; Bell, A.; Nolan, S. P. Tetrahedron 2005, 61, 9716-9722.
26. Nesmeyanov, A. N.; Isaeva, L. S.; Morozova, L. N.; Petrovskii, P. V.; Tumanskii, B. L.; Lokshin, B. V.; Klemenkova, Z. S. Inorg. Chim. Acta 1980, 43, 1-4.
27. For examples, see: (a) Cuvigny, T.; Julia, M. J. Organomet. Chem. 1986, 317, 383-408.
28. (b) Blaser, H. U.; Reinehr, D. Helv. Chim. Acta 1977, 60, 208-210.
29. (c) Soldatov, D. V.; Enright, G. D.; Ripmeester, J. A. Chem. Mater. 2002, 14, 348-356.
30. (d) Sacconi, L.; Mani, F.; Bencini, A. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, U.K., 1987; Vol. 5, p 143.
31. Marion, N.; Ecarnot, E. C.; Navarro, O.; Amoroso, D.; Bell, A.; Nolan, S. P. J. Org. Chem. 2006, 71, 3816-3821.
32. Lintvedt, R. L.; Borer, L. L.; Murtha, D. P.; Kuszaj, J. M.; Glick, M. D. Inorg. Chem. 1974, 13, 18-26.
33. Arduengo, A. J., Ill; Gamper, S. F.; Calabrese, J. C.; Davidson, F. J. Am. Chem. Soc. 1994, 116, 4391-4394.
34. Nicholls, D. In Comprehensive Inorganic Chemistry; TrotmanDickenson, A. F., Ed.; Pergamon Press: Oxford, U.K., 1973; Vol. 3, p 1156.
35. Herrmann, W. A.; Gerstberger, G.; Spiegler, M. Organometallics 1997, 16, 2209-2212.
36. Dorta, R.; Stevens, E. D.; Scott, N. M.; Costabile, C.; Cavallo, L.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2005, 127, 2485-2495.
37. O'Brien, C. J.; Kantchev, E. A. B.; Chass, G. A.; Hadei, N.; Hopkinson, A. C.; Organ, M. G.; Setiadi, D. H.; Tang, T.-H.; Fang, D.-C Tetrahedron 2005, 61, 9723-9735.
38. A recent review: Brookhart, M.; Green, M. L. H.; Parkin, G. Proc. Nat. Acad. Sci. U.S.A. 2007, 104, 6908-6914, and references therein.
39. Huynh, H. V.; Wong, L. R.; Ng, P. S. Organometallics 2008, 27, 2231-2237.
40. (a) Tekavec, T. N.; Louie, J. Tetrahedron 2008, 64, 6870-6875.
41. (b) Youngs, W. J.; Kinder, J. D.; Bradshaw, J. D.; Tessier, C. A. Organometallics 1993, 12, 2406-2407.
42. Titcomb, L. R.; Caddick, S.; Cloke, F. G. N.; Wilson, D. J.; McKerrecher, D. Chem. Commun. 2001, 1388-1389.
43. Calculation of the BDE of la was also tried, but the squarepyramidal structure of la was not stable at the calculation level (B3LYP 6-31G(d,p)).
44. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030-3039.
45. Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029-3036.
46. Arduengo, A. J., III; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
47. Burla, M. C.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Giacovazzo, C.; Polidori, G.; Spagna, R. SIR 2002; 2003.
48. Sheldrick, G. M. SHELXL97-2; 1997.