Copper- or iron-catalyzed arylation of phenols from respectively aryl chlorides and aryl iodides

Chemistry - A European Journal

Volumn 14, Issue 20, 2008, Pages 6037-6039

  Xia, Ning ^a   Taillefer, Marc ^a  

^a INSTITUT CHARLES GERHARDT   (France)

Author keywords

Aryl chlorides; Aryl iodides; Copper; Coupling reactions; Iron

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; COPPER;

ARYL CHLORIDES; ARYL IODIDES; COUPLING REACTIONS; IRON;

PHENOLS;

CHLORIDE; COPPER; IODIDE; IRON; LIGAND; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; CHLORIDES; COPPER; IODIDES; IRON; LIGANDS; MOLECULAR STRUCTURE; PHENOLS;

EID: 51049092766     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800436     Document Type: Article

References (35)

1. a) A. V. Rama Rao, M. K. Gurjar, L. Reddy, A. S. Rao, Chem. Rev. 1995, 95, 2135;
2. b) The Pesticide Manual, 10th ed. (Ed.: C. Tomlin), British Crop Protection Council, Farnham, 1994.
3. a) C. H. Burgos, T. E. Barder, X. Huang, S. L. Buchwald, Angew. Chem. 2006, 118, 4427;
4. Angew. Chem. Int. Ed. 2006, 45, 4321;
5. b) G. Mann, C. Incarvilo, A. L. Rheigold, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 3224;
6. c) S. Harkal, K. Kumar, D. Michalik, A. Zapf, R. Jackstell, F. Rataboul, T. Riemeier, A. Monsees, M. Beller, Tetrahedron Lett. 2005, 46, 3227.
7. a) K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 15, 2428;
8. b) I. P. Belelskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337;
9. c) F. Monnier, M. Taillefer, Angew. Chem. 2008, 120, 3140;
10. Angew. Chem. Int. Ed. 2008, 47, 3096.
11. a) B. H. Lipshutz, J. B. Unger, B. R. Tail, Org. Lett. 2007, 9, 1089;
12. b) A. Ouali, J.-F. Spindler, A. Jutand, M. Taillefer, Adv. Synth. Cat. 2007, 349, 1906;
13. c) A. Ouali, J.-F. Spindler, H.-J. Cristau, M. Taillefer, Adv. Synth. Cat. 2006, 348, 499;
14. d) A. Ouali, R. Laurent, A.-M. Caminade, J.-P. Majorai, M. Taillefer, J. Am. Chem. Soc. 2006, 128, 15990;
15. e) Y. Jin, J. Liu, Y. Yin, H. Fu, Y. Jiang, Y. Zhao, Synlett 2006, 1564;
16. f) Q. Cai, B. Zou, D. Ma, Angew. Chem. 2006, 118, 1298;
17. Angew. Chem. Int. Ed. 2006, 45, 1276;
18. g) H.-J. Cristau, P. P. Cellier, S. Hamada, J.-F. Spindler, M. Taillefer, Org. Lett. 2004, 6, 913;
19. h) D. Ma, Q. Cai, Org. Lett. 2003, 5, 3799;
20. i) E. Buck, Z. J. Song, D. Tschaen, P. G. Dormer, R. P. Volante, P. J. Reider, Org. Lett. 2002, 4, 1623;
21. j) J. Hassan, M. Sévignon, C. Gozzi, E. Schultz, M. Lemaire, Chem. Rev. 2002, 102, 1359;
22. k) R. K. Gujadhur, C. G. Bales, D. Venkataraman, Org. Lett. 2001, 3, 4315;
23. l) A. V. Kalinin, J. F. Bower, P. Riebel, V. Snieckus, J. Org. Chem. 1999, 64, 2986;
24. m) J.-F. Marcoux, S. Doye, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 10539.
25. a) K. Weissermel, H. J. Arpe, Industry Organic Chemistry, Wiley-VCH, Weinheim (Germany), 1997, p. 349.
26. a) M. Taillefer, N. Xia, A. Ouali, US 2006 60/818,334 and PCT 2007/001836;
27. b) M. Taillefer, N. Xia, A. Ouali, Angew. Chem. 2007, 119, 952;
28. Angew. Chem. Int. Ed. 2007, 46, 934.
29. Patented results: N. Xia, M. Taillefer, 2007 US patent 60996830.
30. a) Under similar conditions 4-fluoronitrobenzene reacts more quickly than 4-chloronitrobenzene;
31. b) Related results are known although often following from the use of more activated substrates or metal (Pd)-calalyzed systems: B. Smith, J. March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th ed., Wiley. New York, 2007, p. 853. and references therein.
32. M. Fabre, J. Jaud, M. Hliwa, J.-P. Launay, J. Bonvoisin, Inorg. Chem. 2006, 45, 9332.
33. Very recently the group of Prof. Carsten Bolm obtained similar results in the case of phenyl iodide or of aryl iodides deactivated by electron-donating substituents (O. Bistri, A. Correa, C. Bolm, Angew. Chem. 2008, 120, 596;
34. Angew. Chem. Int. Ed. 2008, 47, 586). In the case of aromatic iodides activated by electron-withdrawing substituents we found under our conditions that the presence of the catalytic system Fe/diketone 1 was not necessary to obtain excellent isolated yields of 2j, 2k, and 21.
35. L. L. J. Winneroski, Y. Xu, J. S. York, patent 2005 WO 05/037763 A1.