Copper-catalyzed amidations of bromo substituted furans and thiophenes

Tetrahedron Letters

Volumn 43, Issue 41, 2002, Pages 7365-7368

  Crawford, Kenneth R ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; COPPER; FURAN; FURAN DERIVATIVE; HALIDE; LIGAND; N,N' DIMETHYLETHYLENEDIAMINE; POTASSIUM CARBONATE; POTASSIUM DIHYDROGEN PHOSPHATE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL PARAMETERS; CHEMICAL REACTION;

EID: 0037037841     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01725-2     Document Type: Article

References (24)

1. . For a recent review of methods for constructing nitrogen heterocycles, see: Nadin A. J. Chem. Soc., Perkin Trans. 1. 1998;3493.
2. Padwa A., Ginn J.D., Bur S.K., Eidell C.K., Lynch S.M. J. Org. Chem. 67:2002;3412.
3. Ginn J.D., Padwa A. Org. Lett. 4:2002;1515.
4. Padwa A., Brodney M.A., Liu B., Satake K., Wu T. J. Org. Chem. 64:1999;3595.
5. Wolfe J.P., Buchwald S.L. J. Org. Chem. 65:2000;1144.
6. Wolfe J.P., Tomori H., Sadighi J.P., Yin J., Buchwald S.L. J. Org. Chem. 65:2000;1158.
7. Harris M.C., Buchwald S.L. J. Org. Chem. 65:2000;5327.
8. Old D.W., Harris M.C., Buchwald S.L. Org. Lett. 2:2000;1403.
9. Antilla J.C., Buchwald S.L. Org. Lett. 3:2001;2077.
10. Hartwig J.F. Angew. Chem., Int. Ed. 37:1998;2047.
11. Hamann B.C., Hartwig J.F. J. Am. Chem. Soc. 120:1998;7369.
12. Mann G., Hartwig J.F., Driver M.S., Fernandez-Rivas C. J. Am. Chem. Soc. 120:1998;827.
13. Hartwig J.F., Kawatsura M., Hauck S.I., Shaughnessy K.H., Alcazar-Roman L.M. J. Org. Chem. 64:1999;5575.
14. Alcazar-Roman L.M., Hartwig J.F., Rheingold A.L., Liable-Sands L.M., Guzei I.A. J. Am. Chem. Soc. 122:2000;4618.
15. Lee S., Jorgensen M., Hartwig J.F. Org. Lett. 3:2001;2729.
16. Yu S., Saenz J., Srirangam J.K. J. Org. Chem. 67:2002;1699.
17. Rivas F.M., Giessert A.J., Diver S.T. J. Org. Chem. 67:2002;1708.
18. Klapars A., Antilla J.C., Huang X., Buchwald S.L. J. Am. Chem. Soc. 123:2001;7727.
19. Luker T.J., Beaton H.G., Whiting M., Mete A., Cheshire D.R. Tetrahedron Lett. 41:2000;7731.
20. Kang S.K., Kim D.H., Park J.H. Synlett. 2002;427.
21. Watanabe M., Yamamoto T., Nishiyama M. J. Chem. Soc., Chem. Commun. 2000;133.
22. All new compounds in this study were fully characterized (IR, NMR, elemental analysis and/or HRMS).
23. A side by side comparison of each diamine ligand generally showed comparable results. One exception was noted with entry 10k, in which a 30% yield was obtained when N,N-dimethyl-trans-cyclohexane diamine was employed.
24. 3, 100 MHz) δ 28.2, 80.4, 104.7, 124.9, 130.6, 141.6 and 152.8.