A β-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions

Journal of Organic Chemistry

Volumn 72, Issue 10, 2007, Pages 3863-3867

  Lv, Xin ^a   Bao, Weiliang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; COPPER; ETHERS; LIGANDS; NUCLEOPHILES; SYNTHESIS (CHEMICAL);

ARYL ETHERS; ARYL THIOETHERS; N-ARYLIMIDAZOLES;

ESTERS;

CARBON; ESTER; NITROGEN; OXYGEN; SULFUR;

ARTICLE; CATALYSIS; CHEMICAL REACTION; LIGAND BINDING; LOW TEMPERATURE; SYNTHESIS;

AMIDES; CARBON; CATALYSIS; COPPER; ESTERS; LIGANDS; MOLECULAR STRUCTURE; NITROGEN; OXYGEN; PYRROLIDINONES; SULFHYDRYL COMPOUNDS; SULFUR;

EID: 34248588689     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070443m     Document Type: Article

References (31)

1. For reviews, see: (a) Barchechath, S. D.; Tawatao, R. I.; Corr, M.; Carson, D. A.; Cottam, H. B. J. Med. Chem. 2005, 48, 6409.
2. (b) Zhong, C; He, J.; Xue, C.; Li, Y. Bioorg. Med. Chem. 2004, 12, 4009.
3. (c) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345.
4. (d) Buckingham, J. B. In Dictionary of Natural Products; CRC Press: Boca Raton, FL, 1994: Vol. 1.
5. For recent copper-catalyzed C-N coupling reactions, see: (a) Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem. 2007, 46, 934.
6. (b) Chen, Y-J.; Chen, H.-H. Org. Lett. 2006, 8, 5609.
7. (c) Buchwald, S. L.; Altman, R. A. Org. Lett. 2006, 8, 2779.
8. (d) Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron 2006, 62, 4435.
9. (e) Zhang, H.; Cai, Q.; Ma, D. W. J. Org. Chem. 2005, 70, 5164.
10. (f) Buchwald, S. L.; Antilla, J. C; Baskin, J. M.; Barder, T. E. J. Org. Chem. 2004, 69, 5578.
11. (g) Cristau, H.-J.; Cellier, P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695. The related applications were earlier reported in a patent in 2001 (FR 01 16547).
12. (h) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
13. (i) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793.
14. (j) Buchwald, S. L.; Klapars, A.; Huang, X. H. J. Am. Chem. Soc. 2002, 124, 7421.
15. For recent C-O coupling reactions, see: (a) Ouali, A.; Spindler, J.-F.; Jutand, A.; Taillefer, M. Organometallics 2007, 26, 65.
16. (b) Ouali, A.; Spindler, J.-F.; Cristau. H. J.; Taillefer, M. Adv. Synth. Catal. 2006, 348, 499.
17. (c) Cristau, H. J.; Cellier, P. P.; Hamada, S.; Spindler, J.-F.; Taillefer, M. Org. Lett. 2004, 6, 913.
18. (d) Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
19. (e) Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 10770.
20. (f) Gujadhur, R. K.; Bates, C G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.
21. For recent C-S coupling reactions, see: (a) ltoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
22. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
23. Shafir, S.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742.
24. Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672.
25. Xie, X.; Chen, Y.; Ma, D. J. Am. Chem. Soc. 2006, 128, 16050.
26. (a) Ouali, A.; Laurent, R.; Caminade, A.-M.; Majorai, J.-P.; Taillefer, M. J. Am. Chem. Soc. 2006,128, 15990.
27. (b) Ouali, A.; Renard, B.; Spindler, J.-F.; Taillefer, M. Chem. - Eur. J. 2006, 20, 5301.
28. (c) Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. - Eur. J. 2006, 12, 3636.
29. (d) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem.-Eur. J. 2004, 10, 5607.
30. (e) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
31. Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.