Low catalyst loadings for copper-catalyzed O-arylation of phenols with aryl and heteroaryl halides under mild conditions

Synlett

Volumn , Issue 1, 2012, Pages 101-106

  Yong, Fui Fong ^a   Teo, Yong Chua ^a   Yan, Yaw Kai ^a   Chua, Guan Leong ^b  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

^b Nanyang Technological University   (Singapore)

Author keywords

copper catalyzed; cross coupling; low catalyst loading; mild conditions; O arylations; phenol

Indexed keywords

2,2,6,6 TETRAMETHYLHEPTANE 3,5 DIONE; ARYL HALOGENIDE; COPPER; HALIDE; HETEROARYL IODIDE; IODIDE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SUBSTITUTION REACTION;

EID: 84655163941     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290110     Document Type: Article

References (34)

1. Evans D A., Devries K M., In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences Vol. 63 Nagarajan R Marcel Decker, Inc. New York 1994 63-104
2. Rao A V., RamaGurjar M K., Reddy L, Rao A S., Chem. Rev. 1995 95 2135
3. Wada C K., Holms J H., Curtin M L., Dai Y, Florjancic A S., Garland R B., Guo Y, Heyman H R., Stacey J R., Steinman D H., Albert D H., Bouska J J., Elmore I N., Goodfellow C L., Marcotte P A., Tapang P, Morgan D W., Michaelides M R., Davidsen S K., J. Med. Chem. 2002 45 219
4. Hodous B L., Feuns-Meyer S D., Hughes P E., Albrecht B K., Bellon S, Bready J, Caenepeel S, Cee V J., Chaffee S C., Coxon A, Emery M, Fretland J, Gallant P, Gu Y, Hoffman D, Johnson R E., Kendall R, Kim J L., Long A M., Morrison M, Olivieri P R., Patel V F., Polverino A, Rose P, Tempest P, Wang L, Whittington D A., Zhao H L., J. Med. Chem. 2007 50 611
5. Liu L B., Siegmund A, Xi N, Kaplan-Lefko P, Rex K, Cheti A, Lin J, Moriguchi J, Berry L, Huang L, Teffera Y, Yang Y I., Zhang Y H., Bellon S F., Lee M, Shimanovich R, Bak A, Dominguez C, Norman M H., Harmange J C., Dussault I, Kimt T S., J. Med. Chem. 2008 51 3688
6. Caron S, Do N M., Sieser J E., Whritenour D C., Hill P D., Org. Process Res. Dev. 2009 13 324
7. Draper W M., Casida J E., J. Agric. Food Chem. 1983 31 1201
8. The Pesticide Manual 10th ed. Tomlin C British Crop Protection Council Farnham 1994
9. Scrano L, Bufo S A., DAuria M, Meallier P, Behechti A, Shramm K W., J. Environ. Qual. 2002 31 268
10. Labadie J W., Hedrick J L., Ueda M, Am. Chem. Soc. Symp. Ser. 1996 624 210
11. Theil F, Angew. Chem. Int. Ed. 1999 38 2345
12. Laskoski M, Dominguez D D., Keller T M., J. Polym. Sci., Part A: Polym. Chem. 2006 44 4559
13. Ullmann F, Chem. Ber. 1904 37 853
14. Lindley J, Tetrahedron 1984 40 1433
15. Paul S, Gupta M, Tetrahedron Lett. 2004 45 8825
16. Marcoux J.-F, Doye S, Buchwald S L., J. Am. Chem. Soc. 1997 119 10539
17. Fagan P F., Hauptman E, Shapiro R, Casalnuovo A, J. Am. Chem. Soc. 2000 122 5043
18. Gujadhur R, Venkataraman D, Synth. Commun. 2001 31 2865
19. Gujadhur R K., Bates C G., Venkataraman D, Org. Lett. 2001 3 4315
20. Ma D, Cai Q, Org. Lett. 2003 5 3799
21. Cai Q, Zou B, Ma D, Angew. Chem. Int. Ed. 2006 45 1276
22. Chen Y.-J, Chen H.-H, Org. Lett. 2006 8 5609
23. Ouali A, Spindler J F., Cristau H J., Taillefer M, Adv. Synth. Catal. 2006 348 499
24. Rao H, Jin Y, Fu H, Jiang Y, Zhao Y, Chem. Eur. J. 2006 12 3636
25. Lv X, Bao W, J. Org. Chem. 2007 72 3863
26. Naidu A B., Raghunath O R., Prasad D J. C., Sekar G, Tetrahedron Lett. 2008 49 1057
27. Niu J, Zhou H, Li Z, Xu J, Hu S, J. Org. Chem. 2008 73 7814
28. Liu Y.-H, Li G, Yang L.-M, Tetrahedron Lett. 2009 50 343
29. Maiti D, Buchwald S L., J. Am. Chem. Soc. 2009 131 17423
30. Zhang Q, Wang D, Wang X, Ding K, J. Org. Chem. 2009 74 7187
31. Maiti D, Buchwald S L., J. Org. Chem. 2010 75 1791
32. Marcoux J.-F, Doye S, Buchwald S L., J. Am. Chem. Soc. 1997 119 10539
33. Buck E, Song Z J., Tschaen D, Dormer P G., Volante R P., Reider P J., Org. Lett. 2002 4 1623
34. Larsson P.-F, Correa A, Carril M, Norrby P.-O, Bolm C, Angew. Chem. Int. Ed. 2009 48 5691