N-tosyloxycarbamates as a source of metal nitrenes: Rhodium-catalyzed C-H insertion and aziridination reactions

Journal of the American Chemical Society

Volumn 127, Issue 41, 2005, Pages 14198-14199

  Lebel, Hélène ^a   Huard, Kim ^a   Lectard, Sylvain ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

METAL DERIVATIVE; N TOSYLOXYCARBAMATE DERIVATIVE; NITROGEN DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; OXIDATION; PHASE TRANSITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

AZIRIDINES; CARBAMATES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM;

EID: 26844569944     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0552850     Document Type: Article

References (43)

1. Recent examples: (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598-600.
2. (b) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
3. (c) Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc: 2004, 126, 15378-15379.
4. (d) Cui, Y.; He, C. Angew. Chem., Int. Ed. 2004, 43, 4210-4212.
5. (a) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935.
6. (b) Merlic, C. A.; Zechman, A. L. Synthesis 2003, 1137-1156.
7. (a) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919-7946.
8. (b) Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050.
9. (c) Maas, G. Chem. Soc. Rev. 2004, 33. 183-190.
10. (a) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861-2903.
11. (b) Davies, H. M. L.; Loe, O. Synthesis 2004, 2595-2608.
12. Kuhn, F. E.; Santos, A. M. Mini-Rev. Org. Chem. 2004, 1, 55-64.
13. 3; see, for example: (a) Bach, T.; Korber, C. Eur. J. Org. Chem. 1999, 1033-1039.
14. (b) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301-3303.
15. See also: (c) Bach, T.; Schlummer, B.; Harms, K. Chem.-Eur. J. 2001, 7, 2581-2594.
16. (d) Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Gotti, C. L.; Lapadula, M.; Mangioni, E.; Cenini, S. Chem.-Eur. J. 2003, 9, 249-259.
17. (a) Abramovitch, R. A.; Davis, B. A. Chem. Rev. 1964, 64, 149-185.
18. (b) Moody, C. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 21.
19. (a) Lwowski, W.; Maricich, T. J. J. Am. Chem. Soc. 1965, 87, 3630-3637.
20. (b) Methcohn, O. Acc. Chem. Res. 1987, 20, 18-27.
21. Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656-3665.
22. Recent examples: (a) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672-13673.
23. (b) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139.
24. (c) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202-16203.
25. (d) Di Chenna, P. H.; Robert-Peillard, F.; Dauban, P.; Dodd, R. H. Org. Lett. 2004, 6, 4503-4505.
26. (e) Leca, D.; Toussaint, A.; Mareau, C.; Fensterbank, L.; Lacote, E.; Malacria, M. Org. Lett. 2004, 6, 3573-3575.
27. (f) Padwa, A.; Flick, A. C.; Leverett, C. A.; Stengel, T. J. Org. Chem. 2004, 69, 6377-6386.
28. Review: Davies, H. M. L.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 3518-3520.
29. (a) Muller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919.
30. (b) Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586.
31. (c) Halfen, J. A. Curr. Org. Chem. 2005, 9, 657-669.
32. For W-arenesulfonyloxycarbamates in other amination processes, see: (a) Greek, C.; Genet, J. P. Synlett 1997, 741-748.
33. (b) Erdik, E. Tetrahedron 2004, 60, 8747-8782.
34. (c) Fioravanti, S.; Morreale, A.; Pellacani, L.; Tardella, P. A. Eur. J. Org. Chem. 2003, 4549-4552 and references therein.
35. (a) Lebel, H. Leogane, O. Org. Lett. 2005. 7, 4107-4110.
36. (b) Lebel, H.; Paquet, V. Organometallics 2004, 23, 1187-1190.
37. (c) Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 320-328.
38. Albone, D. P.; Challenger, S.; Derrick, A. M.; Fillery, S. M.; Irwin, J. L.; Parsons, C. M.; Takada, H.; Taylor, P. C.; Wilson, J. Org. Biomol. Chem. 2005, 3, 107-111.
39. N-tosyloxycarbamates are very easily prepared via tosylation of N-hydroxycarbamates (see Supporting Information for details).
40. Lower catalyst loading led to lower yields (5 mol %:83% yield of 2).
41. 3, and MgO.
42. For X-ray crystal structure, see Supporting Information.
43. Both C-H insertion and aziridination reactions are not sensitive to water, and spectrograde solvent may be used.