An efficient intermolecular BINAM-copper(I) catalyzed Ullmann-type coupling of aryl iodides/bromides with aliphatic alcohols

Tetrahedron Letters

Volumn 49, Issue 19, 2008, Pages 3147-3151

  Naidu, Ajay B ^a   Sekar, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Alkyl aryl ether; Copper catalyst; Coupling reaction; Diamine ligands; Ullmann coupling

Indexed keywords

1,1' BINAPHTHYL 2,2' DIAMINE; ALKANOL; ALKYL ARYL ETHER; AMINE; ARYL IODIDE DERIVATIVE; BROMINE DERIVATIVE; COPPER; IODINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COUPLING FACTOR; SYNTHESIS;

EID: 41649095662     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.015     Document Type: Article

References (29)

1. Yamazaki N., Washio I., Shibasaki Y., and Mitsuru Ueda M. Org. Lett. 8 (2006) 2321-2324
2. Asano M., Inoue M., and Katoh T. Synlett (2005) 2599-2602
3. Jiang H., Leger J.-M., and Huc I. J. Am. Chem. Soc. 125 (2003) 3448-3449
4. Bolm C., Hildebrand J.P., Muñiz K., and Hermanns N. Angew. Chem., Int. Ed. 40 (2001) 3284-3308
5. Gu W.X., Jing X.B., Pan X.F., Chan A.S.C., and Yang T.K. Tetrahedron Lett. 41 (2000) 6079-6082
6. Matsumoto Y., Uchida W., Nakahara H., Yanagisawa I., Shibanuma T., and Nohira H. Chem. Pharm. Bull. 48 (2000) 428
7. Cao B., Park H., and Joullie M.M. J. Am. Chem. Soc. 124 (2002) 520-521
8. Temal-Laïb T., Chastanet J., and Zhu J. J. Am. Chem. Soc. 124 (2002) 583-590
9. Kawata S., and Hirama M. Tetrahedron Lett. 39 (1998) 8707-8710
10. For some recent reports on palladium-catalyzed aryl ether synthesis, see. Vorogushin A.V., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 8146-8149
11. Kataoka N., Shelby Q., Stambuli J., and Hartwig J. J. Org. Chem. 67 (2002) 5553-5566
12. Kuwabe S., Torraca K.E., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 12202-12206
13. Prim D., Campagne J.-M., Joseph D., and Andrioletti B. Tetrahedron 58 (2002) 2041-2075
14. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046-2067
15. Palucki M., Wolfe J.P., and Buchwald S.L. J. Am. Chem. Soc. 119 (1997) 3395-3396
16. Torraca K.E., Huang X., Parrish C., and Buchwald S. J. Am. Chem. Soc. 123 (2001) 10770-10771
17. Shelby Q., Kataoka N., Mann G., and Hartwig J. J. Am. Chem. Soc. 122 (2000) 10718-10719
18. Wolter M., Nordmann G., Job G.E., and Buchwald S.L. Org. Lett. 4 (2002) 973-976
19. Hosseinzadeh R., Tajbakhsh M., Mohajerani M., and Alikarami M. Synlett (2005) 1101-1104
20. Manback G.F., Lipman A.J., Stockland Jr. R.A., Freidl A.L., Hasler A.F., Stone J.J., and Guzei I.A. J. Org. Chem. 70 (2005) 244-250
21. Xiao X.Y., Li R., Hurst D., Zhuang H., Shi S., Czarnik A.W., Robichaud A.J., Wacker D.A., and Robertson D.W. J. Comb. Chem. 4 (2002) 536-539
22. Zhang H., Ma D., and Cao W. Synlett (2007) 243-246
23. Altman R.A., Shafir A.S., Choi A., Lichtor P.A., and Buchwald S.L. J. Org. Chem. 73 (2008) 284-286
24. Mannam S., Kumar S.A., and Sekar G. Adv. Synth. Catal. 349 (2007) 2253-2258
25. Mannam S., and Sekar G. Tetrahedron Lett. 49 (2008) 1083-1086
26. Mannam S., and Sekar G. Tetrahedron Lett. 49 (2008) 2457-2460
27. Naidu A.B., Ragunath O.R., Prasad D.J.C., and Sekar G. Tetrahedron Lett. 49 (2008) 1057-1061
28. 3) δ 14.92, 55.7, 64.06, 114.6, 115.5, 153.1, 153.7.
29. Siegman J.R., and Houser J.J. J. Org. Chem. 47 (1982) 2773-2779