Aliphatic carbon-carbon bond activation of nitriles by rhodium(II) porphyrin

Organometallics

Volumn 26, Issue 1, 2007, Pages 20-21

  Chan, Kin Shing ^a   Li, Xin Zhu ^a   Fung, Chun Wah ^a   Zhang, Lirong ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; MOLECULAR STRUCTURE; ORGANOMETALLICS; PORPHYRINS;

CARBON-CARBON BOND ACTIVATION; LIGANDS; TRANSITION STATE;

RHODIUM COMPOUNDS;

EID: 33846221465     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060828f     Document Type: Article

References (34)

1. Crabtree, R. H. Chem. Rev. 1985, 85, 245-269.
2. (b) Murakami, M.; Ito, Y. In Topics in Organometallic Chemistry; Murai, S., Ed.; Springer: Berlin, 1999; Vol. 3, pp 97-129.
3. (c) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870-883.
4. (d) Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610-618.
5. For a recent review: Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem. 2003, 3513-3526.
6. (a) Miller, J. A. Tetrahedron Lett. 2001, 42, 6991-6993.
7. (b) Miller, J. A.; Dankwardt, J. W. Tetrahedron Lett. 2003, 44, 1907-1910.
8. (c) Miller, J. A.; Dankwardt, J. W.; Penney, J. M. Synthesis 2003, 1643-1648.
9. (d) Penney, J. M.; Miller, J. A. Tetrahedron Lett. 2004, 45, 4989-4992.
10. Nakao, Y.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2004, 126, 13904-13905.
11. Nakazawa, H.; Kamdata, K.; Itazaki, M. Chem. Commun. 2005, 4004-4006.
12. (a) Brunkan, N. M.; Brestensky, D. M.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 3627-3641.
13. (b) García, J. J.; Arévalo, A.; Brunkan, N. M.; Jones, W. D. Organometallics 2004, 23, 3997-4002.
14. (c) Taw, F. L.; Mueller, A. H.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 9808-9813.
15. (d) Lu, T.; Zhuang, X.; Li, Y.; Chen, S. J. Am. Chem. Soc. 2004, 126, 4760-4761.
16. (a) McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493-532.
17. (b) Luo, Y. R. Handbook of Bond Dissociation Energies in Organic Compounds, 1st ed.; CRC Press: Boca Raton, FL, 2003.
18. (a) Wayland, B. B.; Ba, S.; Sherry, A. E. J. Am. Chem. Soc. 1991, 113, 5305-5311.
19. (b) Tse, M. K.; Chan, K. S. Dalton Trans. 2001, 510-511.
20. Zhang, L.; Chan, K. S. J. Organomet. Chem. 2006, 691, 3782-3787.
21. Mak, K. W.; Yeung, S. K.; Chan, K. S. Organometallics 2002, 21, 2362-2364.
22. Formation of a 1:1 Rh(tmp)-ligand complex has been reported: (a) Wayland, B. B.; Sherry, A. E. Bunn, A. G. J. Am. Chem. Soc. 1993, 115, 7675-7684.
23. (b) Collman, J. P.; Boulvtov, R. J. Am. Chem. Soc. 2000, 122, 11812-11821.
24. (a) Ingold, K. U.; Roberts, B. P. Free Radical Substitution Reactions; Wiley: New York, 1971.
25. (b) Davis, A. G.; Roberts, B. P. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, pp 547-589.
26. Pestovsky, O.; Bakac, A. Inorg. Chem. 2002, 15, 3975-3982.
27. Chan, K. S.; Zhang, L.; Fung, C. W. Organometallics 2004, 23, 6097-6098.
28. (a) Cui, W.; Zhang, X. P.; Wayland, B. B. J. Am. Chem. Soc. 2003, 125, 4994-4995.
29. (b) Cui, W.; Wayland, B. B. J. Am. Chem. Soc. 2004, 126, 8266-8274.
30. Giese, B.; Hartung, J.; Kesselheim, C.; Lindner, H. J.; Svoboda, I. Chem. Ber. 1993, 126, 1193-1200.
31. Wayland, B. B.; Balkus, K. J., Jr.; Franos, M. D. Organometallics 1989, 8, 950-955.
32. 3P: i.e., n in eq 3.
33. 2CN is likely sterically hindered.
34. 2CN in 38 and 47%, yields, respectively. These reactions demonstrated the importance of steric effects in coupling.