Mechanism of rhodium-catalyzed carbene formation from diazo compounds

Organic Letters

Volumn 9, Issue 9, 2007, Pages 1663-1665

  Wong, Freeman M ^a   Wang, Jianbo ^c   Hengge, Alvan C ^b   Wu, Weiming ^a  

^a SAN FRANCISCO STATE UNIVERSITY   (United States)

^b UTAH STATE UNIVERSITY   (United States)

^c PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; CARBENE; DRUG DERIVATIVE; HYDROCARBON; METHANE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AZO COMPOUNDS; CATALYSIS; HYDROCARBONS; METHANE; MOLECULAR STRUCTURE; RHODIUM;

EID: 34248343469     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070345n     Document Type: Article

References (32)

1. For reviews, see: (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998.
2. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160.
3. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797-1815.
4. (d) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453.
5. (e) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808.
6. (f) Doyle, M. P. In Homogenous Transition Metal Catalysts in Organic Synthesis; Moser, W. R., Slocum, D. W., Eds.; ACS Advanced Chemistry Series No. 230; American Chemical Society: Washington, DC, 1992.
7. (g) Taber, D. F. In Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 3, p 1045.
8. (h) Doyle, M. P. Chem. Rev. 1986, 86, 919-939.
9. (i) Padwa, A. J. Organomet. Chem. 2001, 617/618, 3-16.
10. For reviews, see: (a) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935.
11. (b) Davies, H. M. L.; Antoulinakis, E. G. J. Organomet. Chem. 2001, 617/618, 47-55.
12. (c) Timmons, D. J.; Doyle, M. P. J. Organomet. Chem. 2001, 617/618, 98-104.
13. (d) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50-61.
14. (a) Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686-7693.
15. (b) Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1994, 116, 8991-9000.
16. (c) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958-964.
17. Yates, P. J. Am. Chem. Soc. 1952, 74, 5376-5381.
18. Maxwell, J. L.; Brown, K. C.; Bartley, D. W.; Kodadek, T. Science 1992, 256, 1544-1547.
19. (a) Aniciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. J. Org. Chem. 1980, 45, 695-702.
20. (b) Alonso, M. E.; Garcia, M.; Del, C. Tetrahedron 1989, 45, 69-76.
21. (c) Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1996, 118, 8162-8163.
22. (d) Pirrung, M. C.; Liu, H.; Morehead, A. T. J., Jr. J. Am. Chem. Soc. 2002, 124, 1014-1023.
23. Qu, Z.; Shi, W.; Wang, J. J. Org. Chem. 2001, 66, 8139-8144.
24. Nowlan, D. T., Ill; Gregg, T. M.; Davies, H. M. L.; Singleton, D. A. J. Am. Chem. Soc. 2003, 125, 15902-15911.
25. Nakamura, E.; Yoshikai, N.; Yamanaka, M. J. Am. Chem. Soc. 2002, 124, 7181-7192.
26. Nowlan, D. T., Ill; Singleton, D. A. J. Am. Chem. Soc. 2005, 127, 6190-6191.
27. Bigeleisen, J. Adv. Chem. Phys. 1958, 1, 15-76.
28. Rao, M.; Barlow, P. N.; Pryor, A. N.; Paneth, P.; O'Leary, M. H.; Quinn, D. M.; Huskey, P. J. Am. Chem. Soc. 1993, 115, 11676-11681.
29. Melander, L.; Saunders, W. H. Reaction Rates of Isotopic Molecules; Wiley: New York, 1980; Chapter 6, pp 170-201.
30. Hengge, A. C.; Stein, R. L. Biochemistry 2004, 43, 742-747.
31. Huskey, W. P. In Enzyme Mechanism from Isotope Effects; Cook, P. F., Ed.; CRC Press: Boca Raton, FL, 1991; pp 37-72.z
32. Brown, L. L.; Drury, J. S. J. Chem. Phys. 1965, 43, 1688-1691.