A new mild regioselective bromination of arylamines

Tetrahedron Letters

Volumn 44, Issue 52, 2003, Pages 9371-9373

  Zhao, Jingrui ^a,b   Jia, Xueshun ^b   Zhai, Hongbin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI UNIVERSITY   (China)

Author keywords

Arylamines; Boron amide; Regioselective bromination

Indexed keywords

AMIDE; AROMATIC AMINE; BORON;

ARTICLE; BROMINATION; LITHIATION; METHODOLOGY; STEREOCHEMISTRY;

EID: 0345304275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.228     Document Type: Article

References (18)

1. Onaka M., Izumi Y. Chem. Lett. 1984;2007-2008.
2. Majetich G., Hicks R., Reister S. J. Org. Chem. 62:1997;4321-4326.
3. Berthelot J., Guette C., Essayegh M., Desbene P.L., Basselier J.J. Synth. Commun. 16:1986;1641-1645.
4. Berthelot J., Guette C., Desbene P.-L., Basselier J.-J. Can. J. Chem. 67:1989;2061-2066.
5. Buckles R.E., Popov A.I., Zelezny W.F., Smith R.J. J. Am. Chem. Soc. 73:1951;4525-4528.
6. Muathen H.A. J. Org. Chem. 57:1992;2740-2741.
7. Cerichelli G., Luchetti L., Mancini G. Tetrahedron Lett. 30:1989;6209-6210.
8. Reeves W.P., King R.M. II. Synth. Commun. 23:1993;855-859.
9. Roy S.C., Guin C., Rana K.K., Maiti G. Tetrahedron Lett. 42:2001;6941-6942.
10. Srivastava S.K., Chauhan P.M.S., Bhaduri A.P. Chem. Commun. 23:1996;2679-2680.
11. Vyas P.V., Bhatt A.K., Ramachandraiah G., Bedekar A.V. Tetrahedron Lett. 44:2003;4085-4088.
12. Smith M.B., Guo L., Okeyo S., Stenzel J., Yanella J., LaChapelle E. Org. Lett. 4:2002;2321-2323.
13. Ando W., Tsumaki H. Synthesis. 1982;263-264.
14. 4), filtered, and concentrated. The residue was purified by silica gel chromatography to afford the bromination product.
15. Compound 7a was prepared in two steps from 2-nitrophenol. See: (a) Fletcher, R. J.; Lampard, C.; Murphy, J. A.; Lewis, N. J. Chem. Soc., Perkin Trans. 1 1995, 6, 623-633; (b) Fusco, R.; Garanti, L.; Zecchi, G. J. Org. Chem. 1975, 40, 1906-1909.
16. Compound 7a was prepared in two steps from 2-nitrophenol. See: (a) Fletcher, R. J.; Lampard, C.; Murphy, J. A.; Lewis, N. J. Chem. Soc., Perkin Trans. 1 1995, 6, 623-633; (b) Fusco, R.; Garanti, L.; Zecchi, G. J. Org. Chem. 1975, 40, 1906-1909.
17. Stella L. Renaud P., Sibi M.P. Radicals in Organic Synthesis. 2:2001;407-426 Wiley-VCH, New York.
18. Bougeois J.-L., Stella L., Surzur J.-M. Tetrahedron Lett. 22:1981;61-64.