Intermolecular coupling reaction of cyclic amines and alkenes catalyzed by a ruthenium-hydride complex (PCy 3) 2(CO)RuHCl

Organometallics

Volumn 23, Issue 23, 2004, Pages 5392-5395

  Yi, Chae S ^a   Yun, Sang Young ^a   Guzei, Ilia A ^b  

^a Marquette University   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC AMINES; INTERMOLECULAR COUPLING; LIGANDS; METAL CATALYSTS;

CATALYSTS; CHEMICAL BONDS; COMPLEXATION; OLEFINS; RUTHENIUM; X RAY CRYSTALLOGRAPHY;

AMINES;

EID: 9144238852     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0401206     Document Type: Article

References (40)

1. Recent reviews: (a) Selective Hydrocarbon Activation; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28,154. (c) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. (d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
2. Recent reviews: (a) Selective Hydrocarbon Activation; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28,154. (c) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. (d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
3. Recent reviews: (a) Selective Hydrocarbon Activation; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28,154. (c) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. (d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
4. Recent reviews: (a) Selective Hydrocarbon Activation; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28,154. (c) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. (d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
5. (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
6. (b) Kakiuchi, F.; Murai, S. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: New York, 1999.
7. Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
8. (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699.
9. (b) Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
10. (c) Kanzelberger, M.; Singh, B.; Czerw, M.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 2000, 122, 11017.
11. (d) Gu, X.-Q.; Chen, W.; Morales-Morales, D.; Jensen, C. M. J. Mol. Catal. (A) 2002, 189, 119.
12. (a) Weissman, H.; Song, X.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 337.
13. (b) Fujiwara, Y.; Jia, C. Pure Appl. Chem. 2001, 73, 319.
14. (c) Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
15. (a) Jun, C.-H.; Hwang, D.-C.; Na, S.-J. Chem. Commun. 1998, 1405.
16. (b) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
17. (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 2685.
18. (b) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964.
19. (a) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935.
20. (b) Ferrando-Miguel, G.; Coalter, J. N., III; Gérard, H.; Huffman, J. C.; Eisenstein, O.; Caulton, K. G. New J. Chem. 2002, 26, 687.
21. (c) Murakami, M.; Hori, S. J. Am. Chem. Soc. 2003, 225, 4720.
22. (d) Zhang, X.; Fried, A.; Knapp, S.; Goldman, A. S. Chem. Commun. 2003, 2060.
23. (e) Lin, Y.; Ma, D.; Lu, X. Tetrahedron Lett. 1987, 28, 3249.
24. (a) Yi, C. S.; He, Z.; Lee, D. W.; Rheingold, A. L.; Lam, K.-C. Organometallics 2000, 19, 2036.
25. (b) Yi, C. S.; He, Z.; Lee, D. W. Organometallics 2001, 20, 802.
26. See the Supporting Information for spectroscopic data of these complexes.
27. (a) Kondo, T.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 2002, 124, 186.
28. (b) Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 126, 12584.
29. (c) Ackermann, L. Organometallics 2003, 22, 4367.
30. (a) Singleton, D. A.; Thomas, A. A. J. Am. Chem. Soc. 1995, 117, 9357.
31. (b) Frantz, D. E.; Singleton, D. A.; Snyder, J. P. J. Am. Chem. Soc. 1997, 119, 3383.
32. Yi, C. S.; He, Z.; Guzei, I. A. Organometallics 2001, 20, 3641.
33. 1H NMR. Also, the addition NaOH did not increase the rate; in fact, addition of an excess amount (>5 equiv to 1) actually reduced the product yield substantially.
34. Yi, C. S.; Lee, D. W. Organometallics 1999, 18, 5152.
35. (a) Huang, D.; Huffman, J. C.; Bollinger, J. C.; Eisenstein, O.; Caulton, K, G. J. Am. Chem. Soc. 1997, 119, 7398.
36. (b) Baratta, W.; Herdtweck, E.; Rigo, P. Angew, Chem., Int. Ed. 1999, 35, 1629.
37. (c) Watson, L. A.; Ozerov, O. V.; Pink, M.; Caulton, K. G. J. Am. Chem. Soc. 2003, 125, 8426.
38. 8b Indeed, this complex was found to be an equally active catalyst under the reaction conditions described in eq 1 (84% 2a).
39. Zhang, J.; Gunnoe, T. B. Organometallics 2003, 22, 2291.
40. Similar ethylene elimination has been commonly observed in metal-catalyzed silylation reactions. Marciniec, B. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 2002; Vol. 1.