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

Synthetic Communications

Volumn 40, Issue 19, 2010, Pages 2954-2962

  Khazaei, Ardeshir ^a   Zolfigol, Mohammad Ali ^a   Kolvari, Eskandar ^b   Koukabi, Nadiya ^a   Soltani, Hamid ^a   Bayani, Leyla Sharaf ^a  

^a BU ALI SINA UNIVERSITY   (Iran)

^b SEMNAN UNIVERSITY   (Iran)

Author keywords

Alkenes; alkynes; aromatic amines; bromination; iodic acid

Indexed keywords

ALKENE; ALKYNE; AROMATIC AMINE; BROMINE; IODATE; IODIC ACID; POTASSIUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; REACTION TIME; ROOM TEMPERATURE;

EID: 77956195653     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903349992     Document Type: Article

References (44)

1. House, H. O. In Modern Synthetic Reactions; W. A. Benjamin (Ed.); Inc.: Menlo Park, CA, 1972; p. 422.
2. Liu, Y. H.; Zhou, S. L. Electrophilic cyclization of 2-(1-alkynyl)-2- alken-1-ones using the I2=K3PO4 system: An efficient synthesis of highly substituted iodofurans. Org. Lett. 2005, 7, 4609-4611.
3. Johnsson, R.; Meijer, A.; Ellervik, U. Mild and efficient direct aromatic iodination. Tetrahedron 2005, 61, 11657-11663.
4. Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Stereoselective debromination of aryl-substituted vic-dibromide with indium metal. Chem. Commun. 1998, 2113-2114.
5. Rieke, R. D.; Sell, M. S. In Handbook of Grignard Reagents; G. S. Silverman, P. E. M. Rakita (Eds.); Dekker: New York, 1996; p. 527.
6. Wakefield, B. J. The Chemistry of Organolithium Compounds; Pergamon Press: Oxford, 1976.
7. Davis, S. G. Organotransition Metal Chemistry: Applications to Organic Synthesis; Pergamon Press: Oxford, 1982.
8. Cannon, K. C.; Krow, G. R. Handbook of Grignard Reagents; Dekker: New York, 1996.
9. Still, J. K. Palladium-catalyzed coupling of organotin reagents with organic electrophiles. Pure Appl. Chem. 1985, 57, 1771-1780.
10. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2843.
11. Beletskaya, I. P.; Cheprakov, A. V. Heck reaction as a sharpening stone of palladium catalysis. Chem. Rev. 2000, 100, 3009-3066.
12. Cabri, W.; Candiani, I. Recent developments and new perspectives in the Heck reaction. Acc. Chem. Res. 1995, 28, 2-7.
13. Butler, A.; Walker, J. V. Marine haloperoxidases. Chem. Rev. 1993, 93, 1937-1944.
14. Bora, U.; Bose, G.; Chaudhuri, M. K.; Dhar, S. S.; Gopinath, R.; Khan, A. T.; Patel, B. K. Regioselective bromination of organic substrates by tetrabutylammonium bromide promoted by V2O5-H2O2: An environmentally favorable synthetic protocol. Org. Lett. 2000, 2, 247-249.
15. Becker, H. G. O. In Organikum: Organisch-chemisches Grundpraktikum; Wiley-VCH: Weinheim, 2001; p. 299.
16. Ryu, I.; Matsubara, H.; Yasuda, S.; Nakamura, H.; Curran, D. P. Phase-vanishing reactions that use fluorous media as a phase screen: Facile, controlled bromination of alkenes by dibromine and dealkylation of aromatic ethers by boron tribromide. J. Am. Chem. Soc. 2002, 124, 12946-12947.
17. Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Stereoselective halogenations of alkenes and alkynes in ionic liquids. Org. Lett. 2001, 3, 1061-1063.
18. Larock, R. C. In Comprehensive Organic Transformation: A Guide to Functional Group Preparation; Wiley-VCH: New York, 1999; p. 629.
19. Dalton, D. R.; Dutta, V. P.; Jones, D. C. Bromohydrin formation in dimethylsulfoxide. J. Am. Chem. Soc. 1968, 90, 5498-5502.
20. Eissen, M.; Lenoir, D. Electrophilic bromination of alkenes: Environmental, health, and safety aspects of new alternative method. Chem. Eur. J. 2008, 14, 9830-9841.
21. Gallou, F.; Reeves, J. T.; Tan, Z. L.; Songa, J. H. J.; Yee, N. K.; Campbell, S.; Jones, P. J.; Senanayake, C. H. Regioselective halogenation of 6-azaindoles: Efficient synthesis of 3-halo-2,3-disubstituted-6-azaindole derivatives. Synlett. 2005, 2400-2402.
22. Moghaddam, F. M.; Boeini, H. Z. Oxidative cyclization of thiobenzanilides to benzothiazoles using N-benzyl-DABCO tribromide under mild conditions. Synlett. 2005, 1612-1614.
23. de Almeida, L. S.; Esteves, P. M.; de Mattos, M. C. S. Tribromoisocyanuric acid: A new reagent for regioselective cobromination of alkenes. Synlett. 2006, 1515-1518.
24. de Almeida, L. S.; Esteves, P. M.; de Mattos, M. C. S. A new regioselective bromination of activated aromatic rings. Synthesis 2006, 221-223.
25. Zolfigol, M. A.; Chehardoli, G.; Salehzadeh, S.; Adams, H.; Ward, M. D. {[K.18-Crown-6]Br-3}(n): A unique tribromide-type and columnar nanotube-like structure for the oxidative coupling of thiols and bromination of some aromatic compounds. Tetrahedron Lett. 2007, 48, 7969-7973.
26. de Almeida, L. S.; Esteves, P. M.; de Mattos, M. C. S. Efficient electrophilic cobromination of alkenes and bromination of activated arenes with bromodichloroisocyanuric acid under mild conditions. Synlett. 2007, 1687-1690.
27. Ying, T. K.; Bao, W. L.; Zhang, Y. M. Bromination of carbon-carbon double bonds involving oxidation of NaBr in an ionic liquid. J. Chem. Res., Synop. 2004, 806-807.
28. Das, B.; Srinivas, Y.; Sudhakar, C.; Damodar, K.; Narender, R. Efficient bromination of alkenes and alkynes using potassium bromide and diacetoxy iodobenzene. Synth. Commun. 2009, 39, 220-227.
29. Moriuchi, T.; Yamaguchi, M.; Kikushima, K.; Hirao, T. An efficient vanadium-catalyzed bromination reaction. Tetrahedron Lett. 2007, 48, 2667-2670.
30. Nair, V.; Panicker, S. B.; Augustine, A.; George, T. G.; Thomas, S.; Vairamani, M. An efficient bromination of alkenes using cerium(IV) ammonium nitrate (CAN) and potassium bromide. Tetrahedron 2001, 57, 7417-7422.
31. Joshi, A. V.; Baidossi, M.; Mukhopadhyay, S.; Sasson, Y. Oxidative bromination of activated aromatic compounds using aqueous nitric acid as an oxidant. Org. Proc. Res. Dev. 2004, 8, 568-570.
32. Muathen, H. A. Mild oxidative bromination of alkenes and alkynes with zinc bromide and lead tetraacetate. Synth. Commun. 2004, 34, 3545-3552.
33. Borikar, S. P.; Daniel, T.; Paul, V. An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3- methylpyridinium tribromide as a new reagent= solvent under mild conditions. Tetrahedron Lett. 2009, 50, 1007-1009.
34. Pilli, R. A.; Robello, L. G. Palladium-catalyzed double cross-coupling of E-vinylic dibromides with PhZnCl and the synthesis of tamoxifen. J. Braz. Chem. Soc. 2004, 15, 938-944.
35. Barhate, N. B.; Gajare, A. S.; Wakharkar, R. D.; Bedekar, A. V. Simple and practical halogenation of arenes, alkenes, and alkynes with hydrohalic acid=H2O2 (or TBHP). Tetrahedron 1999, 55, 11127-11142.
36. Smith, M. B.; Guo, L.; Okeyo, S.; Stenzel, J.; Yanella, J.; LaChapelle, E. Regioselective one-pot bromination of aromatic amines. Org. Lett. 2002, 4, 2321-2323.
37. Hashemi, M. M.; Rahimi, A.; Karimi-Jaberi, Z.; Ahmadibeni, Y. A mild and efficient oxidation of benzylic alcohols without solvent using iodic acid supported on wet Montmorillonite K10 or silica gel under microwave irradiation. Acta Chim. Slov. 2005, 52, 86-87.
38. Choghamarani, A. G. Iodic acid (HIO3). Synlett. 2006, 2347-2348.
39. Hashemi, M. M.; Naeimi, H.; Shirazizadeh, F.; Karimi-Jaberi, Z. Oxidation of a-hydroxy ketones to diketones by iodic acid supported on alumina. J. Chem. Res., Synop. 2006, 345-345
40. Xu, L. A.; Shu, H.; Liu, Y.; Zhang, S. H.; Trudell, M. L. Oxidative cyclization of N-alkylo- methyl-arenesulfonamides to biologically important saccharin derivatives. Tetrahedron 2006, 62, 7902-7910.
41. Zolfigol, M. A.; Bagherzadeh, M.; Niknam, K.; Shirini, F.; Mohammadpoor-Baltork, I.; Choghamarani, A. G.; Baghbanzadeh, M. Oxidation of 1,4-dihydropyridines under mild and heterogeneous conditions using solid acids. J. Iran. Chem. Soc. 2006, 3, 73-80.
42. Zolfigol, M. A.; Shirini, F.; Chehardoli, G.; Kolvari, E. A catalytic and transition-metalfree method for the chemoselective oxidation of alcohols to their corresponding carbonyl compounds using periodic acid or iodic acid in the presence of a catalytic amount of KBr. J. Mol. Catal. A: Chem. 2007, 265, 272-275.
43. Lulinski, P.; Skulski, L. Iodination of both deactivated and activated arenes with sodium periodate or sodium iodate as the oxidants. Bull. Chem. Soc. Jpn. 2000, 73, 951-956.
44. Hashemi, M. M.; Bakhtiari, M.; Karimi-Jaberi, Z. Efficient solvent-free deprotection of acetals and trimethylsilyl ethers with iodic acid on silica gel under microwave irradiation. Russ. J. Org. Chem. 2007, 43, 621-622.