Ligand-free copper(I) catalyzed N- and O-arylation of aryl halides

Tetrahedron Letters

Volumn 48, Issue 41, 2007, Pages 7366-7370

  Sperotto, Elena ^a   de Vries, Johannes G ^b   van Klink, Gerard P M ^a   van Koten, Gerard ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDE DERIVATIVE; BENZYLAMINE; COPPER ION; HALIDE; IMIDAZOLE; PHENOL; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS;

EID: 34548598641     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.026     Document Type: Article

References (44)

1. Buckingham J.B. Dictionary of Natural Products Vol. 1 (1994), CRC Press
2. Craig P.N. In: Drayton C.J. (Ed). Medicinal Chemistry Vol. 8 (1991), Pergamon Press, New York
3. D'Aprano G., Leclerc M., Zotti G., and Schiavon G. Chem. Mater. 7 (1995) 33
4. Bringmann G., Walter R., and Weirich R. Angew. Chem., Int. Ed. 27 (1990) 977
5. Ullmann F. Ber. Dtsch. Chem. Ges. 36 (1903) 2382
6. Ullmann F. Ber. Dtsch. Chem. Ges. 37 (1904) 853
7. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428
8. Sorenson R.J. J. Org. Chem. 65 (2000) 7747
9. Elliot G.I., and Konopelski J.P. Org. Lett. 2 (2000) 3055
10. Antilla J.C., and Buchwald S.L. Org. Lett. 3 (2001) 2077
11. Lam Y.S.P., Vincent G., Clark C.G., Deudon S., and Jadhav P.K. Tetrahedron Lett. 42 (2001) 3415
12. Lam P.Y.S., Deudon S., Averill K.M., Li R., He M.Y., DeShong P., and Clark C.G. J. Am. Chem. Soc. 122 (2000) 7600
13. For reviews, see:. Lindley J. Tetrahedron 40 (1984) 1433
14. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
15. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337
16. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428
17. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727
18. Klapars A., Antilla J.C., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421
19. Kwong F.Y., and Buchwald S.L. Org. Lett. 5 (2003) 793
20. Ma D., Cai Q., and Zhang H. Org. Lett. 5 (2003) 2453
21. Deng W., Wang Y.F., Zou Y., Liu L., and Guo Q.X. Tetrahedron Lett. 45 (2004) 2311
22. Zhang H., Cai Q., and Ma D. J. Org. Chem. 70 (2005) 5164
23. Ma D., Zhang Y., Yao J., Wu S., and Tao F. J. Am. Chem. Soc. 120 (1998) 12459
24. Wolter M., Klapars A., and Buchwald S.L. Org. Lett. 3 (2001) 3803
25. Han C., Shen R., Su S., and Porco J.A. Org. Lett. 6 (2004) 27
26. Evindar G., and Batey R.A. Org. Lett. 5 (2003) 133
27. Goodbrand H.B., and Hu N.-X. J. Org. Chem. 64 (1999) 670
28. Enguehard C., Allouchi H., Gueiffier A., and Buchwald S.L. J. Org. Chem. 68 (2003) 4367
29. Buchwald, S. L.; Klapars, A.; Antilla, J. C.; Job, G. E.; Wolter, M.; Kwong, F. Y.; Nordmann, G.; Hennessy, E. J. Patent WO 02/085838 A1, 2002, CAN 140:181205.
30. Kwong F.Y., Klapars A., and Buchwald S.L. Org. Lett. 4 (2002) 581
31. Ouali A., Taillefer M., Spindler J.-F., and Jutand A. Organometallics 26 (2007) 65
32. Christau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Eur. J. Org. Chem. (2004) 695
33. Christau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Chem. Eur. J. 10 (2004) 5607
34. For examples, see:. Gujadhur R., Venkataraman D., and Kintigh J.T. Tetrahedron Lett. 42 (2001) 4791
35. Gujadhur R., and Venkataraman D. Synth. Commun. 31 (2001) 139
36. Gujadhur R., Bates C.G., and Venkataraman D. Org. Lett. 3 (2001) 4315
37. Jerphagnon T., van Klink G.P.M., de Vries J.G., and van Koten G. Org. Lett. 7 (2005) 5241
38. Sperotto, E.; Jerphagnon, T. ; de Vries, J. G.; van Klink, G. P. M.; van Koten, G., in preparation.
39. Knotter D.M., van Maanen H.L., Grove D.M., Spek A.L., and van Koten G. Inorg. Chem 30 (1991) 3309
40. Sperotto, E.; van Klink, G. P. M.; van Koten, G. Organic Syntheses, submitted.
41. CuCl and CuBr were freshly prepared according to literature procedures, see:. Richardson H.W. Handbook of Copper Compounds and Applications (1997), Pibro-Tech, Inc., Sumter pp 53-92
42. Chamber C., and Hilliday A.K. Modern Inorganic Chemistry (1975), Rhadon, Butterworths pp 408-416
43. Cotton F.A., Wilkinson G., Murillo C.A., and Bochmann M. Advanced Inorganic Chemistry (1999), John Wiley&Sons 854-876
44. CuCl and CuBr salts show low air stability. However, the same results in terms of the yield of product were achieved when the reaction mixtures were prepared in air.