Expanding the scope of C-H amination through catalyst design

Journal of the American Chemical Society

Volumn 126, Issue 47, 2004, Pages 15378-15379

  Espino, Christine G ^a   Fiori, Kristin Williams ^a   Kim, Mihyong ^a   Du Bois, J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFANILAMIDE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; MOLECULAR INTERACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 9644254037     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0446294     Document Type: Article

References (33)

1. For recent reviews on C-H amination, see: (a) Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586. (b) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, and 2905-2920.
2. For recent reviews on C-H amination, see: (a) Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586. (b) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, and 2905-2920.
3. (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598-600.
4. (b) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
5. (c) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950-12951.
6. (d) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.
7. (e) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.
8. (f) Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed. 2004, 43, 4349-4352.
9. (a) Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233-2236.
10. (b) Au, S.-M.; Huang, J.-S.; Che, C.-M.; Yu, W.-Y. J. Org. Chem. 2000, 65, 7858-7864.
11. (c) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem. - Eur. J. 2002, 8, 1563-1572.
12. (d) Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Che, C.-M. J. Org. Chem. 2004, 69, 3610-3619.
13. Espino, C. G.; Brodsky, B. H.; Kim, M.; Du Bois, J. Manuscript in preparation.
14. Doyle, M. P.; Ren, T. Prog. Inorg. Chem. 2001, 49, 113-168 and references therein.
15. 2+ dimers, see: (a) Bickley, J.; Bonar-Law, R.; McGrath, T.; Singh, N.; Steiner, A. New J. Chem. 2004, 28, 425-433. Also see: (b) Gallagher, J. F.; Ferguson, G.; McAlees, A. J. Acta Crystallogr. 1997, C53, 576-579. (c) Bonar-Law, R. P.; McGrath, T. D.; Singh, N.; Bickley, J. F.; Femoni, C.; Steiner, A. J. Chem. Soc., Dalton Trans. 2000, 4343-4347.
16. 2+ dimers, see: (a) Bickley, J.; Bonar-Law, R.; McGrath, T.; Singh, N.; Steiner, A. New J. Chem. 2004, 28, 425-433. Also see: (b) Gallagher, J. F.; Ferguson, G.; McAlees, A. J. Acta Crystallogr. 1997, C53, 576-579. (c) Bonar-Law, R. P.; McGrath, T. D.; Singh, N.; Bickley, J. F.; Femoni, C.; Steiner, A. J. Chem. Soc., Dalton Trans. 2000, 4343-4347.
17. 2+ dimers, see: (a) Bickley, J.; Bonar-Law, R.; McGrath, T.; Singh, N.; Steiner, A. New J. Chem. 2004, 28, 425-433. Also see: (b) Gallagher, J. F.; Ferguson, G.; McAlees, A. J. Acta Crystallogr. 1997, C53, 576-579. (c) Bonar-Law, R. P.; McGrath, T. D.; Singh, N.; Bickley, J. F.; Femoni, C.; Steiner, A. J. Chem. Soc., Dalton Trans. 2000, 4343-4347.
18. The effectiveness of the tethered dicarboxylate Rh dimers for carbene and nitrene transfer is consistent with a carboxylate shift mechanism recently suggested by Corey: Lou, Y.; Horikawa, M.; Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916-8918.
19. Taber, D. F.; Meagley, R. P.; Louey, J. P.; Rheingold, A. L. Inorg. Chim Acta 1995, 239, 25-28.
20. (a) Davies, H. M. L. Eur. J. Org. Chem. 1999, 2459-2469.
21. (b) Davies, H. M. L.; Venkataramani, C. Org. Lett. 2003, 5, 1403-1406.
22. This ligand has been shown to bridge a diferric complex: Beer, R. H.; Tolman, W. B.; Bott, S. G.; Lippard, S. J. Inorg. Chem. 1989, 28, 4557-4559.
23. See Supporting Information for details.
24. Cui, Y.; He, C. Angew. Chem., Int. Ed. 2004, 43, 4210-4212.
25. Espino, C. G. Ph.D. Thesis, Stanford University, Stanford, CA, 2004.
26. 4 afforded product yields below 40%. A full account of studies with urea and sulfamide substrates will be forthcoming.
27. For alternative methods to cyclic sulfamides and applications thereof, see: (a) Nicolaou, K. C.; Longbottom, D. A.; Snyder, S. A.; Nalbanadian, A. Z.; Huang, X. Angew. Chem., Int. Ed. 2002, 41, 3866-3870 and references therein, (b) Régaïnia, Z.; Winum, J.-Y.; Smaine, F.-Z.; Toupet, L.; Aouf, N.-E.; Montera, J.-L. Tetrahedron 2003, 59, 6051-6056.
28. For alternative methods to cyclic sulfamides and applications thereof, see: (a) Nicolaou, K. C.; Longbottom, D. A.; Snyder, S. A.; Nalbanadian, A. Z.; Huang, X. Angew. Chem., Int. Ed. 2002, 41, 3866-3870 and references therein, (b) Régaïnia, Z.; Winum, J.-Y.; Smaine, F.-Z.; Toupet, L.; Aouf, N.-E.; Montera, J.-L. Tetrahedron 2003, 59, 6051-6056.
29. For representative papers, see: (a) Mahy, J. P.; Bedi, G.; Battioni, P.; Mansuy, D. Tetrahedron Lett. 1988, 29, 1927-1930. (b) Nageli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087-1105. (c) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507-4510. (d) Díaz-Requejo, M. M.; Belderraín, T. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2003, 125, 12078-12079.
30. For representative papers, see: (a) Mahy, J. P.; Bedi, G.; Battioni, P.; Mansuy, D. Tetrahedron Lett. 1988, 29, 1927-1930. (b) Nageli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087-1105. (c) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507-4510. (d) Díaz-Requejo, M. M.; Belderraín, T. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2003, 125, 12078-12079.
31. For representative papers, see: (a) Mahy, J. P.; Bedi, G.; Battioni, P.; Mansuy, D. Tetrahedron Lett. 1988, 29, 1927-1930. (b) Nageli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087-1105. (c) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507-4510. (d) Díaz-Requejo, M. M.; Belderraín, T. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2003, 125, 12078-12079.
32. For representative papers, see: (a) Mahy, J. P.; Bedi, G.; Battioni, P.; Mansuy, D. Tetrahedron Lett. 1988, 29, 1927-1930. (b) Nageli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087-1105. (c) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507-4510. (d) Díaz-Requejo, M. M.; Belderraín, T. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2003, 125, 12078-12079.
33. We have employed 14 previously for intermolecular olefin aziridination reactions. For a convenient preparation, see: Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672-13673.