Efficient bromination of alkenes and alkynes using potassium bromide and diacetoxy iodobenzene

Synthetic Communications

Volumn 39, Issue 2, 2009, Pages 220-227

  Das, Biswanath ^a   Srinivas, Yallamalla ^a   Sudhakar, Chittaluri ^a   Damodar, Kongara ^a   Narender, Ravirala ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Alkene; Alkyne; DIB; trans dibromo compound

Indexed keywords

ALKENE; ALKYNE; DIACETOXY IODOBENZENE; IODOBENZENE; POTASSIUM BROMIDE; UNCLASSIFIED DRUG;

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

EID: 58149131313     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801979379     Document Type: Article

References (16)

1. House, H. O. Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin Inc., Menlo Park, CA, 1972; p. 422.
2. Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Stereoselective debromination of aryl-substituted vic-dibromide with indium metal. Chem. Commun. 1998, 2113.
3. Rieke, R. D.; Sell, M. S. In Handbook of Grignard Reagents; G. S. Silverman and P. E. M. Rakita (Eds.); Dekker: New York, 1996; Chap. 26, p. 527.
4. Fieser, L. F.; Fieser, M. Reagents for Organic Synyhesis; Wiley: New York, 1967: Vol. 1, p. 967.
5. Berthelot, J.; Benammar, Y.; Lange, C. A mild and efficient sonochemical bromination of alkenes using tetrabutylammonium tribromide. Tetrahedron Lett. 1991, 32, 4135.
6. Hazra, G.; Chordia, M. D.; Bahule, B. B.; Pore, V. S.; Basu, S. Manganese-mediated novel dibromination of olefins with tetradecyltrimethylammonium permanganate and trimethylbromosilane. J. Chem. Soc., Perkin Trans. 1, 1994, 1667.
7. 2 (or TBHP). Tetrahedron 1999, 55, 11127.
8. Rodebaugh, R.; Dahenham, J. S.; Fraser-Reid, B.; Snyder, J. P. Bromination of alkenyl glycosides with copper(II) bromide and lithium bromide: Synthesis, mechanism, and DFT calculations. J. Org. Chem, 1999, 64, 1758.
9. 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.
10. Moriuchi, T.; Yamaguchi, M.; Kikushimia, K.; Hirao, T. An efficient vanadium-catalyzed bromination reaction. Tetrahedron Lett. 2007, 48, 2667.
11. Das, B.; Venkateswarlu, K.; Mahender, G.; Mahender, I. A simple and efficient method for α -bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst. Tetrahedron Lett. 2005, 46, 3041.
12. Das, B.; Ramu, R.; Ravikanth, B.; Reddy, K. R. Regioselective ring-opening of aziridines with potassium thiocyanate and thiols using sulfated zirconia as a heterogeneous recyclable catalyst. Tetrahedron Lett. 2006, 47, 779.
13. Das, B.; Venkateswarlu, K.; Krishnaiah, M.; Synthesis of β-chlorohydrins in water Helv. Chim. Acta 2007, 90, 149.
14. Varvoglis, A. Hypervalent Iodine in Organic Synythesis; Academic: New York, 1997.
15. Wirth, T. Hypervalent iodine chemistry: Modern development in organic synthesis, In Topics in Current Chemistry; Springer: Berlin, 2003: p. 224.
16. Das, B.; Holla, H.; Mahender, G.; Banrjee, J.; Reddy, M. R. Hypervalent iodine-mediated interaction of aldoximes with activated alkenes including Baylis-Hillman adducts: A new and efficient method for the preparation of nitrile oxides from aldoximes. Tetrahedron Lett. 2004, 45, 7347.