Chemo-selective copper-catalyzed C-O coupling reactions of phenols with aryl/vinyl halides using enaminone as efficient ligand

Applied Organometallic Chemistry

Volumn 26, Issue 8, 2012, Pages 445-447

  Wan, Jie Ping ^a   Wang, Chunping ^a   Liu, Yunyun ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

aryl ethers; C O; copper catalysis; coupling; enaminone; ligand; vinyl ethers

Indexed keywords

ARYL ETHER; AS-LIGANDS; CHEMOSELECTIVE; COPPER CATALYSIS; COUPLING REACTION; ENAMINONES; VINYL ETHERS;

CATALYSIS; COPPER; COUPLINGS; ETHERS; ORGANIC COMPOUNDS; PHENOLS;

LIGANDS;

EID: 84864479654     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.2886     Document Type: Article

References (33)

1. F. Ullmann, Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
2. I. Goldberg, Ber. Dtsch. Chem. Ges. 1906, 39, 1691.
3. I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337.
4. K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 2428.
5. a) F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 2008, 47, 3096.
6. b) F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 2009, 48, 6954.
7. a) Y. Liu, J.-P. Wan, Org. Bio. Chem. 2011, 9, 6873.
8. b) Y. Liu, J.-P. Wan, Chem. Asian J. 2012, in press, DOI: 10.1002/asia.2011 01063.
9. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054.
10. G. Evano, M. Toumi, A. Coste, Chem. Commun. 2009, 4166.
11. J. C. Antilla, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 11684.
12. D. Ma, Y. Zhang, J. Yao, S. Wu, F. Tao, J. Am. Chem. Soc. 1998, 120, 12459.
13. A. Shafir, S. L. Buchwald, J. Am. Chem. Soc. 2006, 128, 8742.
14. X. Lv, W. Bao, J. Org. Chem. 2007, 72, 3863.
15. R. A. Altman, S. L. Buchwald, Org. Lett. 2006, 8, 2779.
16. H. J. Crisau, P. P. Cellier, J.-F. Sindler, M. Taillefer, Chem. Eur. J. 2004, 10, 5607.
17. A. B. Naidu, G. Sekar, Tetrahedron Lett. 2008, 49, 3147.
18. A. K. Verma, J. Singh, V. K. Sankar, R. Chaudhary, R. Chandra, Tetreharon Lett. 2007, 48, 4207.
19. L. Liu, M. Frohn, N. Xi, C. Domingures, R. Hungate, P. J. Reider, J. Org. Chem. 2005, 70, 10135.
20. H. Ma, X. Jiang, J. Org. Chem. 2007, 72, 8943.
21. D. Wang, K. Ding, Chem. Commun. 2009, 1891.
22. D. Cheng, F. Gan, W. Qian, W. Bao, Green Chem. 2008, 10, 171.
23. M. S. Kabir, M. Lorenz, O. A. Namjoshi, J. M. Cook, Org. Lett. 2010, 12, 464.
24. L. Li, L. Zhu, D. Chen, X. Hu, R. Wang, Eur. J. Org. Chem. 2011, 2692.
25. Q. Cai, B. Zou, D. Ma, Angew. Chem. Int. Ed. 2006, 45, 1276.
26. N. Xia, M. Taillefer, Chem. Eur. J. 2008, 14, 6307.
27. E. Sprotto, G. P. M. van Klink, J. G. de Vries, G. van Koten, Tetrahedron 2010, 66, 9009.
28. Q. Zhang, D. Wang, X. Wang, K. Ding, J. Org. Chem. 2009, 74, 7187.
29. B. Screedhar, R. Arundhathi, P. L. Reddy, M. L. Kantam, J. Org. Chem. 2009, 74, 7951.
30. S. Jammi, S. Sakthivel, L. Rout, T. Mukherjee, S. Mandal, R. Mitra, P. Saha, T. Punniyamurthy, J. Org. Chem. 2009, 74, 1971.
31. C. Cheng, G. Sun, J. Wan, C. Sun, Synlett 2009, 2663.
32. R. Xu, J.-P. Wan, H. Mao, Y. Pan, J. Am. Chem. Soc. 2010, 132, 15531.
33. J.-P. Wan, C. Wang, Y. Liu, Org. Biomol. Chem. 2011, 9, 6481.