Highly efficient copper catalytic system for the O-arylation of phenol with iodoarene

Tetrahedron Letters

Volumn 53, Issue 1, 2012, Pages 71-75

  Cheng, An Yi ^a   Hsieh, Jen Chieh ^a  

^a TAMKANG UNIVERSITY   (Taiwan)

Author keywords

1H imidazole 4 carboxylic acid; Cu2O; Diaryl ether; O arylation; Ullmann coupling

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; COPPER; FUNCTIONAL GROUP; IMIDAZOLE DERIVATIVE; IODINE DERIVATIVE; OXYGEN; PHENOL;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; QUANTUM YIELD; REACTION ANALYSIS;

EID: 82955237471     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.149     Document Type: Article

References (26)

1. For selected papers: J. Zhu Synlett 1997 133 144
2. A.J. Zhang, and K. Burgess Angew. Chem., Int. Ed. 38 1999 634 636
3. T. Eicher, S. Fey, W. Puhl, E. Büchel, and A. Speicher Eur. J. Org. Chem. 1998 877 888
4. D. Maiti, and S.L. Buchwald J. Org. Chem. 75 2011 1791 1794
5. For selected papers: M.S. Lee, and S.Y. Kim Macromol. Rapid Commun. 26 2005 52 56
6. F. Wang, M. Hickner, Y.S. Kim, T.A. Zawodzinski, and J.E. McGrath J. Membr. Sci. 197 2002 231 242
7. F. Theil Angew. Chem., Int. Ed. 38 1999 2345 2347
8. F. Ullmann Ber. Dtsch. Chem. Ges. 37 1904 853 857
9. E. Buck, Z.J. Song, D. Tschaen, P.G. Dormer, R.P. Volante, and P. Reider J. Org. Lett. 4 2002 1623 1626
10. A.B. Naidu, E.A. Jaseer, and G. Sekar J. Org. Chem. 74 2009 3675 3679
11. E. Sperotto, G.P.M. van Klink, J.G. de Vries, and G. van Koten Tetrahedron 66 2010 9009 9020
12. For selected papers: N. Xia, and M. Taillefer Chem. Eur. J. 14 2008 6037 6039
13. R. Zhang, J. Liu, S. Wang, J. Niu, C. Xia, and W. Sun ChemCatChem 3 2011 146 149
14. R.A. Altman, and S.L. Buchwald Org. Lett. 9 2007 643 646
15. S.V. Ley, and A.W. Thomas Angew. Chem., Int. Ed. 42 2003 5400 5449
16. G. Evano, N. Blanchard, and M. Toumi Chem. Rev. 108 2008 3054 3131
17. N.R. Jogdand, B.B. Shingate, and M.S. Shingare Tetrahedron Lett. 50 2009 4019 4021
18. Y.-J. Chen, and H.-H. Chen Org. Lett. 8 2006 5609 5612
19. A. Ouali, J.-F. Spindler, A. Jutand, and M. Taillefer Adv. Synth. Catal. 349 2007 1906 1916
20. D. Ma, and Q. Cai Org. Lett. 5 2003 3799 3802
21. Q. Cai, G. He, and D. Ma J. Org. Chem. 71 2006 5268 5273
22. H. Rao, Y. Jin, H. Fu, Y. Jiang, and Y. Zhao Chem. Eur. J. 2006 3636 3646
23. H.-J. Cristau, P.P. Cellier, S. Hamada, J.-F. Spindler, and M. Taillefer Org. Lett. 6 2004 913 916
24. Y.-H. Liu, G. Li, and L.-M. Yang Tetrahedron Lett. 50 2009 343 346
25. Although the copper catalyzed cross-coupling reactions were mostly carried out with high catalyst loadings, some conditions with low catalyst loadings were also reported: S.L. Buchwald, and C. Bolm Angew. Chem., Int. Ed. 48 2009 5586 5587
26. P.-F. Larsson, A. Correa, M. Carril, P.-O. Norrby, and C. Bolm Angew. Chem., Int. Ed. 48 2009 5691 5693