A general and mild Ullmann-type synthesis of diaryl ethers

Organic Letters

Volumn 6, Issue 6, 2004, Pages 913-916

  Cristau, Henri Jean ^a   Cellier, Pascal P ^a   Hamada, Samy ^a   Spindler, Jean Francis ^a,b   Taillefer, Marc ^a  

^a Lab de Chimie Organique   (France)

^b Rhodia Europe   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; BROMIDE; CESIUM; CESIUM CARBONATE; COPPER DERIVATIVE; COPPER OXIDE; ETHER DERIVATIVE; IODIDE; LIGAND; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 1642528362     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036290g     Document Type: Article

References (42)

1. Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345.
2. (a) Zhu, J. Synlett 1997, 133.
3. (b) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544.
4. The Pesticide Manual, 10th ed.; Tomlin, C., Ed.; Crop Protection Publications: Farnham, UK, 1994.
5. For reviews, see: (a) Sawyer, J. S. Tetrahedron 2000, 56, 5045. (b) Lindley, J. Tetrahedron 1984, 40, 1433. (c) Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679. (d) Reference 1.
6. For reviews, see: (a) Sawyer, J. S. Tetrahedron 2000, 56, 5045. (b) Lindley, J. Tetrahedron 1984, 40, 1433. (c) Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679. (d) Reference 1.
7. For reviews, see: (a) Sawyer, J. S. Tetrahedron 2000, 56, 5045. (b) Lindley, J. Tetrahedron 1984, 40, 1433. (c) Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679. (d) Reference 1.
8. For reviews, see: (a) Sawyer, J. S. Tetrahedron 2000, 56, 5045. (b) Lindley, J. Tetrahedron 1984, 40, 1433. (c) Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679. (d) Reference 1.
9. (a) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
10. (b) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553 and references therein.
11. (c) Ding, S.; Gray, N. S.; Ding, Q.; Schultz, P. G. Tetrahedron Lett. 2001, 42, 8751.
12. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1904, 37, 853.
13. (b) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
14. (c) Thomas, A. W.; Ley, S. V. Angew. Chem. Int. Ed. 2003, 42, 5400.
15. (a) Tomita, M.; Fujitani, K.; Aoyagi, Y. Chem. Pharm. Bull. 1965, 13, 1341.
16. (b) Jung, M. E.; Jachiet, D.; Rohloff, J. C. Tetrahedron Lett. 1989, 30, 4211.
17. (a) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
18. (b) Goodbrand, H. B.; Hu, N.-X. J. Org. Chem. 1999, 64, 670.
19. (c) Lu, Z.; Twieg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 6289.
20. (a) Weingarten, H. J. Org. Chem. 1964, 29, 3624.
21. (b) Oi, R.; Shimakawa, C.; Takenaka, S. Chem. Lett. 1988, 899.
22. (c) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043.
23. (d) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
24. (e) Gujadhur, R. K.; Venkataraman, D. Synth. Commun. 2001, 31, 2865.
25. (f) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.
26. Kiyomori, A.; Marcoux, J.-F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
27. Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
28. (a) Chan, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863.
29. (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
30. Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381.
31. (a) Barton, D. H. R.; Finet, J.-P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619.
32. (b) Barton, D. H. R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1987, 28, 887.
33. Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695-709.
34. These results, obtained more than two years ago, appear only now in the literature due to the regular time required for patent protection. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR Patent 2833947 (WO Patent 03/050885), Rhodia Chimie, 2003; Chem. Abstr. 2003, 139, 69290. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. Patent priority number FR 03 10253. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Ouali, A. Patent priority number FR 02 06717 (International application number PCT/FR03/01647), Rhodia Chimie, 2003.
35. These results, obtained more than two years ago, appear only now in the literature due to the regular time required for patent protection. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR Patent 2833947 (WO Patent 03/050885), Rhodia Chimie, 2003; Chem. Abstr. 2003, 139, 69290. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. Patent priority number FR 03 10253. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Ouali, A. Patent priority number FR 02 06717 (International application number PCT/FR03/01647), Rhodia Chimie, 2003.
36. These results, obtained more than two years ago, appear only now in the literature due to the regular time required for patent protection. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR Patent 2833947 (WO Patent 03/050885), Rhodia Chimie, 2003; Chem. Abstr. 2003, 139, 69290. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. Patent priority number FR 03 10253. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Ouali, A. Patent priority number FR 02 06717 (International application number PCT/FR03/01647), Rhodia Chimie, 2003.
37. Stabilized form sold by Aldrich was used.
38. For a discussion of the so-called "cesium effect"; see: (a) Dijkstra, G.; Kruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1987, 52, 4230. (b) Galli, C. Org. Prep. Proced. Int. 1992, 24, 287.
39. For a discussion of the so-called "cesium effect"; see: (a) Dijkstra, G.; Kruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1987, 52, 4230. (b) Galli, C. Org. Prep. Proced. Int. 1992, 24, 287.
40. Thermal decomposition of cesium hydrogen carbonate produced during the coupling leads to the formation of water or cesium hydroxide, as underlined by Greiner: Greiner, A. Synthesis 1989, 312. For an example of such byproduct formation, see: Beletskaya, I. P.; Davydov, D. V.; Gorovoi, M. S.; Kardashov, S. V. Russ. Chem. Bull. 1999, 48, 1533.
41. Thermal decomposition of cesium hydrogen carbonate produced during the coupling leads to the formation of water or cesium hydroxide, as underlined by Greiner: Greiner, A. Synthesis 1989, 312. For an example of such byproduct formation, see: Beletskaya, I. P.; Davydov, D. V.; Gorovoi, M. S.; Kardashov, S. V. Russ. Chem. Bull. 1999, 48, 1533.
42. 2, and filtered through a plug of Celite. The solvent was removed in vacuo to yield the crude product, which was purified by silica gel chromatography.