Mild conditions for copper-catalyzed coupling reaction of phenols and aryl iodides and bromides

Advanced Synthesis and Catalysis

Volumn 348, Issue 4-5, 2006, Pages 499-505

  Ouali, Armelle ^a   Spindler, Jean Francis ^b   Cristau, Henri Jean ^a   Taillefer, Marc ^a  

^a INSTITUT CHARLES GERHARDT   (France)

^b Rhodia Europe   (France)

Author keywords

Aryl bromides; Catalysis; Copper; N ligands; Phenol; Tripotassium phosphate

Indexed keywords

EID: 33645943023     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200505385     Document Type: Article

References (60)

1. a) F. Ullmann, P. Sponagel, Justus Liebigs Ann. Chem. 1906, 350, 83-107;
2. b) F. Ullmann, H. Kipper, Ber. dtsch. chem. Ges. 1905, 38, 2120-2126;
3. c) F. Ullmann, P. Sponagel, Ber. dtsch. chem. Ges. 1905, 38, 2211-2212;
4. d) F. Ullmann, Ber. dtsch. chem. Ges. 1904, 37, 853-854.
5. a) S. Chowdhury, P. E. Georghiou, J. Org. Chem. 2001, 66, 6257-6262;
6. b) D. L. Boger, M. A. Patane, J. Zhou, J. Am. Chem. Soc. 1994, 116, 8544-8556;
7. c) K. Smith, D. Jones, J. Chem. Soc., Perkin Trans 1 1992, 407-408;
8. d) D. L. Oger, S. M. Sakya, D. Yohannes, J. Org. Chem. 1991, 56, 4204-4207;
9. e) D. L. Boger, D. Yohannes, J. Org. Chem. 1991, 56, 1763-1767;
10. f) D. L. Boger, D. Yohannes, J. Org. Chem. 1990, 55, 6000-6017;
11. g) D. A. Evans, J. A. Ellman, J. Am. Chem. Soc. 1989, 111, 1063-1072;
12. h) M. E. Jung, D. Jachiet, J. C. Rohloff, Tetrahedron Lett. 1989, 30, 4211-4214;
13. i) M. Nogradi, B. Vermes, M. Kajtar-Peredy, Tetrahedron Lett. 1987, 28, 2899-2900;
14. j) T. Yamamoto, Y. Kurata, Can. J. Chem. 1983, 61, 86-91;
15. k) V. V. Litvak, S. M. Shein, J. Org. Chem. USSR 1975, 11, 92-96;
16. l) M. Tomita, K. Fujitani, Y. Aoyagi, Chem. Pharm. Bull. 1965, 13, 1341-1345;
17. m) R. G. R. Bacon, H. A. O. Hill, J. Chem. Soc. 1964, 1108-1112;
18. n) P. A. Sartoretto, F. J. Sowa, J. Am. Chem. Soc. 1937, 59, 603-606.
19. a) M. E. Jung, L. S. Starkey, Tetrahedron 1997, 53, 8815-8824;
20. b) J. Zhu, Synlett 1997, 133-144;
21. c) A. Becker, Inventory of Industrial Fluoro-Biochemicals, Editions Eyrolles, Paris, 1996;
22. d) A. V. Rama Rao, M. K. Gurjar, L. Reddy, A. S. Rao, Chem. Rev. 1995, 95, 2135-2167;
23. e) The Pesticide Manual, 10th edn., (Ed.: C. Tomlin), Crop Protection Publications, The British Crop Protection Council & The Royal Society of Chemistry, 1994;
24. f) R. F. Pellon, R. Carrasco, V. Milian, L. Rodés, Synth. Commun. 1995, 25, 1077-1083.
25. F. Theil, Angew. Chem. Int. Ed. 1999, 38, 2345-2347.
26. For reviews, see: a) K. Kunz, U. Scholtz, D. Ganzer, Synlett 2003, 2428-2439;
27. b) S. V. Ley, A. W. Thomas, Angew. Chem. Int. Ed. 2003, 42, 5400-5449.
28. a) A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4369-4378;
29. b) G. Mann, J. F. Hartwig, Tetrahedron Lett. 1997, 38, 8005-8008;
30. c) G. Mann, C. Incarvito, A. L. Rheingold, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 3224-3225;
31. d) Q. Shelby, N. Kataoka, G. Mann, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 10718-10719;
32. e) N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566;
33. f) S. Ding, N. S. Gray, Q. Ding, P. G. Schultz, Tetrahedron Lett. 2001, 42, 8751-8755.
34. a) R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, M. Alikarami, Synlett 2005, 1101-1104;
35. b) D. Ma, Q. Cai, Org. Lett. 2003, 5, 3799-3802;
36. c) E. Buck, Z. J. Song, D. Tschaen, P. G. Dormer, R. P. Volante, P. J. Reider, Org. Lett. 2002, 4, 1623-1626;
37. d) J. Hassan, M. Sévignon, C. Gozzi, E. Schultz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469;
38. e) R. K. Gujadhur, D. Venkataraman, Synth. Commun. 2001, 31, 2865-2879;
39. f) R. K. Gujadhur, C. G. Bates, D. Venkataraman, Org. Lett. 2001, 3, 4315-4317;
40. g) P. J. Fagan, E. Hauptman, R. Shapiro, A. Casalnuovo, J. Am. Chem. Soc. 2000, 122, 5043-5051;
41. h) V. Snieckus, A. V. Kalinin, J. F. Bower, P. Riebel, J. Org. Chem. 1999, 64, 2986-2987;
42. i) J.-F. Marcoux, S. Doye, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 10539-10540.
43. For patents, see: a) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, French Patent FR 2833947, 2003; Chem. Abstr. 2003, 139, 69290;
44. b) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, World Patent WO 03/050885, 2003;
45. c) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, French Patent FR 2840303, 2003; Chem. Abstr. 2004, 140, 16744;
46. d) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, A. Ouali, World Patent WO 03/101966, 2003;
47. e) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, French Patent priority number FR 03 10253, 2004;
48. f) J.-F. Spindler, M. Taillefer, H.-J. Cristau, P. P. Cellier, A. Ouali, World Patent WO 2005023731, 2005.
49. For applications of our copper-based catalytic systems, see: a) H.-J. Cristau, A. Ouali, J.-F. Spindler, M. Taillefer, Chem. Eur-J. 2005, 11, 2483-2492;
50. b) H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Org. Lett. 2004, 6, 913-916;
51. c) H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Eur. J. Org. Chem. 2004, 695-709;
52. d) H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Chem. Eur. J.l 2004, 10, 5607-5622.
53. For a discussion of the so-called "cesium effect", see: a) G. Dijkstra, W. H. Kruizinga, R. M. Kellogg, J. Org. Chem. 1987, 52, 4230-4234;
54. b) C. Galli, Org. Prep. Proced. Int. 1992, 24, 287-307.
55. [8c] but it was not shown that such turnovers could be reached in the case of this reaction.
56. a) E. J. Hennessy, S. L. Buchwald, Org. Lett. 2002, 4, 269-272;
57. b) F. Y. Kwong, A. Klapars, S. L. Buchwald, Org. Lett. 2002, 4, 581-584.
58. A. A. Moroz, M. S. Shvartsberg, Russ. Chem. Rev. 1974, 43, 679-689.
59. R. K. Dieter, L. A. Silks III, J. R. Fishpaugh, M. E. Kastner, J. Am. Chem. Soc. 1985, 101, 4679-4692.
60. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, 3rd edn., Pergamon Press, New York, 1985.