Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion

Journal of the American Chemical Society

Volumn 128, Issue 28, 2006, Pages 9048-9049

  Thu, Hung Yat ^a   Yu, Wing Yiu ^a,b   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLPYRIDINE; 2 PYRROLIDONE DERIVATIVE; 3 BROMOBENZYL ALDEHYDE; 4 IODOACETOPHENONE O METHYL OXIME; ACETAMIDE DERIVATIVE; ACETOPHENONE DERIVATIVE; ALKANE DERIVATIVE; AMIDE; BENZALDEHYDE DERIVATIVE; BENZAMIDE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBON; HYDROGEN; N METHYLFORMAMIDE; NITROGEN; OXIDIZING AGENT; PALLADIUM; PYRIDINE DERIVATIVE; SUCCINIMIDE DERIVATIVE; SULFONAMIDE; TRANSITION ELEMENT; TRIFLUOROACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYSIS; CATALYST; CHELATION; CHEMICAL BOND; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 33746071928     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062856v     Document Type: Article

References (33)

1. (a) Struff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586.
2. (b) Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560.
3. (c) Davies, H. M. L.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 3518.
4. (d) Huang, X.; Anderson K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
5. (e) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
6. (a) Leung, S. K.-Y.; Tsui, W.-M.; Huang, J.-S.; Che, C.-M.; Liang, J.-L.; Zhu, N. J. Am. Chem. Soc. 2005, 127, 16629.
7. (b) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563.
8. (c) Liang, J.-L.; Yuan, S.-X.; Huang, J.-L.; Yu, W.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2002, 41, 3465.
9. (d) Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C.-M. J. Am. Chem. Soc. 1999, 121, 1, 9120.
10. (a) Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378.
11. (b) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672.
12. (c) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
13. (d) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
14. (a) Hamilton, C. W.; Laitar, D. S.; Sadighi, J. P. Chem Commun. 2004, 1628.
15. (b) Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Li Gotti, C.; Lapadula, M.; Magioni, E.; Cenini, S. Chem.-Eur. J. 2003, 9, 249.
16. (c) Diaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2003, 125, 12078.
17. (a) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
18. (b) Catellani, M.; Chiusoli, G. P.; Costa, M. J. Organomet. Chem. 1995, 500, 69.
19. (c) Ryabov, A. D. Synthesis 1985, 233.
20. (a) Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
21. (b) Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790.
22. (c) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
23. (d) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
24. 2-catalyzed chelation-assisted C-H activation: (a) Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78.
25. (b) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem, Soc. 2005, 127, 13154.
26. (c) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
27. (d) Sezen, B.; Franz, R.; Sames, D. J. Am. Chem. Soc. 2002, 124, 13372.
28. 2 afforded the product amide 2e-A5 in 79% yield without any chlorination products.
29. 2Ar]" complex.
30. Canty, A. J.; Denney, M. C.; Koten, G.; Skelton, B. W.; White, A. H. Organometallics 2004, 23, 5432.
31. (a) Anandhi, H.; Holbert, T.; Lueng, D.; Sharp, P. R. Inorg. Chem. 2003, 42, 1282.
32. (b) Besenyei, G.; Párkányi, L.; Foch, I.; Simándi, L. I. Angew. Chem., Int. Ed. 2000, 39, 956.
33. (c) Moiseev, I. I.; Stromnova, T. A.; Vargaftik, M. N.; Orlova, S. T.; Chernysheva, T. V.; Stoloarv, I. P. Catal. Today 1999, 51, 595.