K3PO4-catalyzed regiospecific aminobromination of βnitrostyrene derivatives with N-Bromoacetamide as aminobtominating agent

Journal of Organic Chemistry

Volumn 75, Issue 6, 2010, Pages 2085-2088

  Chen, Zhan Guo ^a,b   Wang, Yun ^a,b   Wei, Jun Fa ^a,b   Zhao, Peng Fei ^a,b   Shi, Xian Ying ^a,b  

^a SHAANXI NORMAL UNIVERSITY   (China)

^b Key Laboratory for Macromolecular Science of Shaanxi Province   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CONJUGATE ADDITION; N-BROMOACETAMIDE; NITROSTYRENE; REGIOSPECIFIC; ROOM TEMPERATURE;

BROMINE; CHEMICAL REACTIONS;

INERT GASES;

3,5 DIMETHOXY BETA NITROSTYRENE; ACETAMIDE DERIVATIVE; N BROMOACETAMIDE; NITROSTYRENE; POTASSIUM DIHYDROGEN PHOSPHATE; SOLVENT; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; AMINE; BETA-NITROSTYRENE; BROMINE; DICHLOROMETHANE; N-BROMOACETAMIDE; PHOSPHATE; POTASSIUM DERIVATIVE;

AMINOBROMINATION; ARTICLE; BROMINATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; HALOGENATION; X RAY ANALYSIS; CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ACETAMIDES; AMINES; BROMINE; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; METHYLENE CHLORIDE; MOLECULAR STRUCTURE; PHOSPHATES; POTASSIUM COMPOUNDS; STEREOISOMERISM; STYRENES;

EID: 77949945951     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9026879     Document Type: Article

References (44)

1. Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol.3, pp 471-513.
2. For a recent review, see: Li, G.; Saibabu Kotti, S. R. S.; Timmons, C. Eur. J. Org. Chem. 2007, 2745-2758.
3. (a) Daniher, F. A.; Butler, P. E. J. Org. Chem. 1968, 33, 4336.
4. (b) Daniher, F. A.; Butler, P. E. J. Org. Chem. 1968, 33, 2637-2642.
5. (c) Daniher, F. A.; Melchior, M. T.; Butler, P. E. Chem. Commun. 1968, 931-932.
6. (d) Yeung, Y.-Y.; Gao, X.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 9644-9645.
7. (a) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 5863-5864.
8. (b) Driguez, H.; Vermes, J. P.; Lessard, J. Can. J. Chem. 1978, 56, 119-130.
9. (c) Lessard, J.; Driguez, H.; Vermes, J. P. Tetrahedron Lett. 1970, 11, 4887-4890.
10. (d) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045-4048.
11. Qui, J.; Silverman, R. B. J. Med. Chem. 2000, 43, 706-720.
12. (a) Wu, X.-L.; Wang, G.-W. J. Org. Chem. 2007, 72, 9398-9401.
13. (b) Wu, X.-L.; Xia, J.-J.; Wang, G.-W. Org. Biomol. Chem. 2008, 6, 548-553.
14. (c) Liu, J.-Y.; Wang, Y.-N.; Li, G. Eur. J. Org. Chem. 2006, 3112-3115.
15. (d) Timmons, C.; Chen, D.-J.; Xu, X.; Li, G. Eur. J. Org. Chem. 2003, 3850-3854.
16. (e) Ma, L.; Du, D.-M.; Xu, J.-X. J. Org. Chem. 2005, 70, 10155-10158.
17. (a) Li, G.; Kim, S.-H.; Wei, H.-X. Tetrahedron Lett. 2000, 41, 8699-8703.
18. (b) Li, G.; Wei, H.-X.; Kim, S.-H. Tetrahedron 2001, 57, 8407-8411.
19. (c) Li, G.; Wei, H.-X.; Kim, S.-H. Org. Lett. 2000, 2, 2249-2252.
20. (d) Zhi, S.; Han, J.; Lin, C.; An, G.; Pan, Y.; Li, G. Synthesis 2008, 10, 1570-1574.
21. (e) Kotti, S. R. S. S.; Xu, X.; Wang, Y.-N.; Headley, A. D.; Li, G. Tetrahedron Lett. 2004, 45, 7209-7212.
22. Han, J.-L.; Zhi, S.-J.; Wang, L.-Y.; Pan, Y.; Li, G. Eur. J. Org. Chem. 2007, 1332-1337.
23. (a) Wang, Y-N.; Ni, B.; Headley, A. D.; Li, G. Adv. Synth, Catal. 2007, 349, 319-322.
24. (b) Chen, D.-L; Guo, L.; Liu, J.-Y.; Kirtane, S.; Cannon, J. F.; Li, G. Org. Lett. 2005, 7, 921-924.
25. (c) Han, J.-L.; Li, Y.-F.; Zhi, S.-J.; Pan, Y.; Timmons, C.; Li, G. Tetrahedron 2006, 47, 7225-7228.
26. (d) Wang, Y.-N.; Kattuboina, A.; Ai, T.; Banerjee, D.; Li, G. Tetrahetron Lett. 2007, 48, 7894-7898.
27. Phukan, P.; Chakraborty, P.; Kataki, D. J. Org. Chem. 2006, 71, 7533-7537.
28. Thakur, V. V.; Talluri, S. K.; Sudalai, A. Org. Lett. 2003, 5, 861-864.
29. Wu, X.-L.; Wang, G-W. J. Org. Chem. 2007, 72, 9398-9401.
30. Minakata, S.; Yoneda, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2006, 8, 967-969.
31. (a) Chen, Z.-G.; Wei, J.-F.; Li, R.-T.; Shi, X.-Y.; Zhao, P.-F. J. Org. Chem. 2009, 74, 1371-1373.
32. (b) Wei, J.-F.; Chen, Z.-G.; Lei, W.; Zhang, L.-H.; Wang, M.-Z.; Shi, X.-Y.; Li, R.-T. Org. Lett. 2009, 11, 4216-4219.
33. (c) Chen, Z.-G.; Wei, J.-F.; Wang, M.-Z.; Zhou, L.-Y.; Zhang, C.-J.; Shi, X.-Y. Adv. Synth, Catal. 2009, 351, 2358-2368.
34. (d) Wei, J.-F.; Zhang, L.-H.; Chen, Z.-G.; Shi, X.- Y.; Cao, J.-J. Org. Biomol. Chem. 2009, 7, 3280-3284.
35. (a) Enders, D.; Wiedemann. J. Synthesis 1996, 1443-1450.
36. (b) Lucet, D.; Toupet, L.; Gall, T. L.; Mioskowski, C. J. Org. Chem. 1997, 62, 2682-2683.
37. Rank, W.; Baer, H. H. Tetrahedran Lett. 1974, 1459-1462.
38. Qi, X.; Lee, S.-H.; Kwon, J. Y.; Kim, Y.; Kim, S.-J.; Lee, Y.-S.; Yoon, J. J. Org. Chem. 2003, 68, 9140-9143.
39. (a) Bourguignon, J.; LeNard, G.; Queguiner, G. Can. J. Chem. 1985, 63, 2354-2361.
40. (b) McAnda, A. F.; Roberts, K. D.; Smallridge, A. J.; Ten, A.; Trewhella, M. A. J. Chem. Soc., Perkin Trans. 1 1998, 501-504.
41. (c) Liu, J.-T.; Yao, C.-F. Tetrahedron Lett. 2001, 42, 6147-6150.
42. (d) Bowman, R. K.; Johnson, J. S. J. Org. Chem. 2004, 69, 8537-8540.
43. Eugene P. O.; Corinne G. Org. Synth. 1951, 31, 17.
44. Organic Syntheses; Wiley; New York, 1963; Collect. Vol.IV, pp 104.