Elctrophilic bromination of alkenes, alkynes, and aromatic amines with potassium bromide/orthoperiodic acid under mild conditions

Synthesis

Volumn , Issue 21, 2009, Pages 3672-3676

  Khazaei, Ardeshir ^a   Zolfigol, Mohammad Ali ^a   Kolvari, Eskandar ^b   Koukabi, Nadiya ^a   Soltani, Hamid ^a   Komaki, Fatemeh ^a  

^a BU ALI SINA UNIVERSITY   (Iran)

^b SEMNAN UNIVERSITY   (Iran)

Author keywords

Alkenes; Aromatic amines; Bromination; Orthoperiodic acid

Indexed keywords

ALKENES; AROMATIC AMINES; BROMO COMPOUNDS; ROOM TEMPERATURE; SHORT REACTION TIME;

ACETYLENE; ACIDS; AMINATION; AROMATIC COMPOUNDS; DICHLOROMETHANE; OLEFINS; POTASSIUM; POTASSIUM COMPOUNDS;

AMINES;

ALKENE; ALKYNE; AROMATIC AMINE; BENZYLIDENEACETONE; PERIODIC ACID; POTASSIUM BROMIDE;

ARTICLE; BROMINATION; REACTION TIME; ROOM TEMPERATURE; SYNTHESIS;

EID: 72049107500     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216994     Document Type: Article

References (42)

1. House, H. O. In Modern Synthetic Reactions; W. A. Benjamin Inc.: Menlo Park, CA, 1972, 422.
2. Liu, Y. H.; Zhou, S. L. Org. Lett. 2005, 7, 4609.
3. Johnsson, R.; Meijer, A.; Ellervik, U. Tetrahedron 2005, 61, 11657.
4. Rannu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113.
5. Rieke, R. D.; Sell, M. S. In Handbook of Grignard Reagents; Silverman, G. S.; Rakita, P. E. M., Eds.; Dekker: New York, 1996, 527.
6. Normant, H. Adv. Org. Chem. 1960, 2, 1.
7. Wakefield, B. J. The Chemistry of Organolithium Compounds; Pergamon Press: Oxford, 1976.
8. Davis, S. G. Organotransition Metal Chemistry: Applications to Organic Synthesis; Pergamon Press: Oxford, 1982.
9. Cannon, K. C.; Krow, G. R. Handbook of Grignard Reagents; Dekker: New York, 1996.
10. Still, J. K. Pure Appl. Chem. 1985, 57, 1771.
11. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
12. Beletskaya, I. P.; Cheprakov, A. V. Chem, Rev. 2000, 100, 3009.
13. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
14. Butler, A.; Walker, J. V. Chem. Rev. 1993, 93, 1937.
15. Bora, U.; Bose, G.; Chaudhuri, M. K.; Dhar, S. S.; Gopinath, R.; Khan, A. T.; Patel, B. K. Org. Lett. 2000, 2, 247.
16. Becker, H. G. O.; Beckert, R.; Domschke, G.; Fanghänel, E.; Habicher, W. D.; Metz, P.; Pavel, D.; Schwetlich, K. In Organikum: Organisch-chemisches Grundpraktikum, 21st ed.; Wiley-VCH: Weinheim, 2001, 299.
17. Ryu, I.; Matsubara, H.; Yasuda, S.; Nakamura, H.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 12946.
18. ( 18) Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Org. Lett. 2001, 5, 1061.
19. Larock, R. C. In Comprehensive Organic Transformation: A Guide to Functional Group Preparation; Wiley-VCH: New York, 1999, 629.
20. Dalton, D. R.; Dutta, V. P.; Jones, D. C. J. Am. Chem. Soc. 1968, 90, 5498.
21. The Merck Index, 13th ed.; Whitehouse Station: New York, 2001.
22. Eissen, M.; Lenoir, D. Chem. Eur. J. 2008, 14, 9830.
23. Gallou, F.; Reeves, J. T.; Tan, Z. L.; Songa, J. H. J.; Yee, N. K.; Campbell, S.; Jones, P. J.; Senanayake, C. H. Synlett 2005, 2400.
24. Moghaddam, F. M.; Boeini, H. Z. Synlett 2005, 1612.
25. de Almeida, L. S.; Esteves, P. M.; de Mattos, M. C. S. Synlett 2006, 1515.
26. de Almeida, L. S.; Esteves, P. M.; de Mattos, M. C. S. Synthesis 2006, 221.
27. Zolfigol, M. A.; Chehardoli, G. A.; Salehzadeh, S.; Adams, H.; Ward, M. J. Mol. Cotal. A: Chem. 2007, 48, 7969.
28. de Almeida, L. S.; Esteves, P. M.; de Mattos, M. C. S. Synlett 2007, 1687.
29. Ying, T. K.; Bao, W. L.; Zhang, Y. M. J. Chem. Res., Synop. 2004, 806.
30. Das, B.; Srinivas, Y.; Sudhakar, C.; Damodar, K.; Narender, R. Synth. Commun. 2009, 39, 220.
31. Moriuchi, T.; Yamaguchi, M.; Kikushima, K.; Hirao, T. Tetrahedron Lett. 2007, 48, 2667.
32. Nair, V.; Panicker, S. B.; Augustine, A.; George, T. G.; Thomas, S.; Vairamani, M. Tetrahedron 2001, 57, 7417.
33. Joshi, A. V.; Baidossi, M.; Mukhopadhyay, S.; Sasson, Y. Org. Process Res. Dev. 2004, 8, 568.
34. Kim, S. S.; Nehru, K.; Kim, S. S.; Kim, D. W.; Jung, H. C. Synthesis 2002, 52, 2484.
35. Kim, S. S.; Nehru, K. Synlett 2002, 616.
36. Kim, S. S.; Trushkov, I.; Sar, S. K. Bull. Korean Chem. Soc. 2002, 23, 1331.
37. Bruce, A. H.; Kristen, L. W.; Mark, E. M. Synth. Commun. 2007, 37, 3855.
38. Sosnowski, M.; Skulski, L. Molecules 2000, 10, 401.
39. Sosnowski, M.; Skulski, L.; Wolowik, K. Molecules2004, 9, 617.
40. Zheng, L.; Run, B. D.; Yu, L. X.; Sheng, Y. S. Synth. Commun. 2005, 35, 2515.
41. Zolfigol, M. A.; Bagherzadeh, M.; Mallakpour, S.; Chehardoli, G.; Ghorbani-Choghamarani, A.; Koukabi, N.; Dehghanian, M.; Doroudgar, M. J. Mol. Catal. A: Chem. 2007, 270, 219.
42. Zolfigol, M. A.; Shirini, F.; Chehardoli, G.; Kolvari, E. J. Mol. Catal. A: Chem. 2007, 265, 272.