An efficient approach to 2-bromoalken-3-ols by regioselective bromohydroxylation reaction of simple allenes with NBS

European Journal of Organic Chemistry

Volumn , Issue 12, 2011, Pages 2278-2285

  Kong, Wangqing ^a   Guo, Binjie ^a   Fu, Chunling ^a   Ma, Shengming ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Allenes; Bromine; Bromohydroxylation; Electrophilic addition; Regioselectivity

Indexed keywords

EID: 79953718412     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001676     Document Type: Article

References (42)

1. I. Cabanal-Duvillard, J. Berrien, J. Royer, H. Husson, Tetrahedron Lett. 1998, 39, 5181.
2. K. Rossen, R. A. Reamer, R. P. Volante, P. J. Reider, Tetrahedron Lett. 1996, 37, 6843.
3. L. Mévellec, M. Evers, F. Huet, Tetrahedron 1996, 52, 15103.
4. D. T. Sawyer, J. P. Hage, A. Sobkowiak, J. Am. Chem. Soc. 1995, 117, 106.
5. H. Fu, H. Kondo, Y. Ichikawa, G. C. Look, C. Wong, J. Org. Chem. 1992, 57, 7265.
6. J. Lai, F. Wang, G. Guo, L. Dai, J. Org. Chem. 1993, 58, 6944.
7. R. Rodebaugh, B. Fraser-Reid, J. Am. Chem. Soc. 1994, 116, 3155.
8. M. Yamashita, A. Iida, K. Ikai, T. Oshikawa, T. Hanaya, H. Yamamoto, Chem. Lett. 1992, 407.
9. T. Kato, T. Hirukawa, K. Namiki, Tetrahedron Lett. 1992, 33, 1475.
10. For halohydroxylation reactions of 1,2-allenyl sulfoxides and sulfones, see
11. S. Ma, Q. Wei, H. Wang, Org. Lett. 2000, 2, 3893.
12. S. Ma, H. Ren, Q. Wei, J. Am. Chem. Soc. 2003, 125, 4817.
13. C. Zhou, C. Fu, S. Ma, Tetrahedron 2007, 63, 7612.
14. G. He, H. Guo, R. Qian, Y. Guo, C. Fu, S. Ma, Tetrahedron 2009, 65, 4877.
15. G. He, C. Fu, S. Ma, Tetrahedron 2009, 65, 8035.
16. For halohydroxylation reactions of 1,2-allenyl sulfides or selenides, see
17. S. Ma, X. Hao, X. Huang, Org. Lett. 2003, 5, 1217.
18. S. Ma, X. Hao, X. Meng, X. Huang, J. Org. Chem. 2004, 69, 5720.
19. S. Ma, X. Hao, X. Huang, Chem. Commun. 2003, 1082.
20. For halohydroxylation reactions of 1,2-allenylfuranones, see:, Z. Gu, Y. Deng, W. Shu, S. Ma, Adv. Synth. Catal. 2007, 349, 1653.
21. S. Ma, Acc. Chem. Res. 2009, 42, 1679.
22. H. G. Peer, Recl. Trav. Chim. Pays-Bas 1962, 81, 113, for other reports, see
23. W. H. Mueller, P. E. Butler, K. Griesbaum, J. Org. Chem. 1967, 32, 2651.
24. M. L. Poutsma, J. Org. Chem. 1968, 33, 4080.
25. K. Griesbaum, W. Naegele, G. Wanless, J. Am. Chem. Soc. 1965, 87, 3151, for recations with HCl, see
26. T. L. Jacobs, R. N. Johnson, J. Am. Chem. Soc. 1960, 82, 6397.
27. W. H. Mueller, P. E. Butler, J. Org. Chem. 1968, 33, 1533, for the reaction of phenylpropadienes, see
28. K. Izawa, T. Okuyama, T. Fueno, J. Am. Chem. Soc. 1973, 95, 4090.
29. M. Okutani, Y. Mori, J. Org. Chem. 2009, 74, 442.
30. X. Jiang, C. Fu, S. Ma, Eur. J. Org. Chem. 2010, 687.
31. C. Kosinski, A. Hirsch, F. W. Heinemann, F. Hampel, Eur. J. Org. Chem. 2001, 3879.
32. B. Lü, C. Fu, S. Ma, Tetrahedron Lett. 2010, 51, 1284.
33. J.-L. Moreau, M. Gaudemar, J. Organomet. Chem. 1976, 108, 159.
34. Crabbé, B. Nassim, M. T. Robert-Lopes, Org. Synth. 1985, 63, 203.
35. L. Brandsma, H. D. Verkuijsse, Synthesis of Acetylenes, Allenes and Cumulenes, Elsevier, Amsterdam, 1981.
36. E. J. Corey, H. A. Krist, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1970, 92, 6314.
37. K. A. Parker, T. Iqbal, J. Org. Chem. 1987, 52, 4369.
38. P. D'Arrigo, C. Fuganti, G. Pedrocchi Fantoni, S. Servi, Tetrahedron 1998, 54, 15017.
39. W. R. Bowman, C. F. Bridge, P. Brookes, M. O. Cloonan, D. C. Leach, J. Chem. Soc. Perkin Trans. 1 2002, 58.
40. G. C. Nwokogu, J. Org. Chem. 1985, 50, 3900.
41. A. Burger, S. E. Zimmerman, E. J. Ariens, J. Med. Chem. 1966, 9, 469.
42. C. U. Pittman Jr., G. A. Olah, J. Am. Chem. Soc. 1965, 87, 5632.