Cyclometalation reactions involving C-Cl bond activation of ortho-chlorinated substrates with imine as anchoring groups by cobalt complexes

Organometallics

Volumn 27, Issue 2, 2008, Pages 270-275

  Chen, Yue ^a   Sun, Hongjian ^a   Flörke, Ulrich ^b   Li, Xiaoyan ^a  

^a SHANDONG UNIVERSITY   (China)

^b UNIVERSITY OF PADERBORN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHEMICAL BONDS; CONDENSATION; METAL COMPLEXES; REACTION KINETICS; X RAY DIFFRACTION ANALYSIS;

COBALT COMPLEXES; CYCLOMETALATION REACTIONS; ORTHO-CHELATED COBALT(III) COMPLEX;

COBALT;

EID: 38949202626     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7008793     Document Type: Article

References (48)

1. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
2. Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367-2370.
3. (a) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478.
4. (b) Hooper, M. W.; Hartwig, J. F. Organometallics 2003, 22, 3394-3403.
5. (c) Hooper, M. W.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861-2873.
6. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387-3388.
7. (b) Littke, A. F.; Fu, G. C Angew. Chem., Int. Ed. 1999, 38, 2411-2413.
8. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
9. (a) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378.
10. (b) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
11. (c) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413-2416.
12. (d) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162-1163.
13. (e) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655.
14. (f) Walker, S. D.; Barder, T. E.; Martinelli, J. R; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871-1876.
15. (g) De Lewis, A. K.; Caddick, S.; Cloke, F. G. N.; Billingham, N. C.; Hitchcock, P. B.; Leonard, J. J. Am. Chem. Soc. 2003, 125, 10066-10073.
16. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 11818-11819.
17. Gstöttmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1363-1365.
18. (a) Chen, C.; Yang, L.-M. Tetrahedron Lett. 2007, 48, 2427-2430.
19. (b) Galland, J.-C.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 2323-2326.
20. (c) Indolese, A. F. Tetrahedron Lett. 1997, 38, 3513-351.
21. (d) Saito, S.; Ohtani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024-8030.
22. (a) Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1700.
23. (b) Korn, T. J.; Cahiez, G.; Knochel, P. Synlett. 2003, 1892.
24. (c) Korn, T. J.; Cahiez, G.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 2947-2951.
25. (a) Avedissian, H.; Brillon, L.; Cahiez, G.; Knochel, P. Tetrahedron Lett. 1998, 39, 6163.
26. (b) Cahiez, G.; Avedissian, H. Tetrahedron Lett. 1998, 39, 6159.
27. (a) For an excellent review see: Shinokubo, H.; Oshima, K. Eur. J. Org. Chem. 2004, 2081.
28. (b) Fujioka, T.; Nakamura, T.; Yorimitsu, H.; Oshima, K. Org. Lett. 2002, 4, 2257.
29. (c) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem. 2002, 114, 4311;
30. Angew. Chem., Int. Ed. 2002, 41, 4137.
31. (d) Wakabayashi, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 5374.
32. (e) Ohmiya, H.; Tsuji, T.; Yorimitsu, H.; Oshima, K. Chem.-Eur. J. 2004, 10, 5640.
33. (f) Ikeda, Y.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2002, 124, 6514.
34. (g) Mizutani, K.; Shinokubo, H.; Oshima, K. Org. Lett. 2003, 5, 3959.
35. (a) Gomes, P.; Gosmini, C.; Prichon, J. Org. Lett. 2003, 5, 1043.
36. (b) Gomes, P.; Gosmini, C.; Prichon, J. Synthesis 2003, 1909.
37. Fornies, J.; Green, M.; Spencer, J. L.; Gordon, F.; Stone, G. A. J. Chem. Soc., Dalton Trans. 1997, 1006.
38. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2004, 126, 3068.
39. Macgregor, S. A.; Roe, D. C.; Marshall, W. J.; Bloch, K. M.; Bakhmutov, V. I.; Grushin, V. V. J. Am. Chem. Soc. 2005, 127, 15304.
40. Caubere, V. V. Rev. Heteroatom. Chem. 1991, 4, 78.
41. Grushin, V. V.; Alper, H. Top. Organomet. Chem. 1999, 3, 193.
42. (a) Klein, H.-F.; Camadanli, S.; Beck, R.; Leukel, D.; Flörke, U. Angew. Chem., Int. Ed. 2005, 44, 975.
43. (b) Klein, H.-F.; Camadanli, S.; Beck, R.; Flörke, U. Chem. Commun. 2005, 381-382.
44. Li, X.; Sun, H.; Yu, F.; Flörke, U.; Klein, H.-F. Organometallics 2006, 25, 4695.
45. Klein, H.-F.; Karsch, H. H. Chem. Ber. 1976, 109, 1453.
46. Dönnecke, D.; Haibauer, K.; Imhof, W. J. Organomet. Chem. 2004, 689, 2707.
47. Klein, H.-F.; Karsch, H. H. Chem. Ber. 1975, 108, 944-955.
48. Klein, H.-F.; Karsch, H. H. Inorg. Chem. 1975, 14, 473-477.