Reductive bromine atom-transfer reaction

Organic Letters

Volumn 15, Issue 11, 2013, Pages 2826-2829

  Sumino, Shuhei ^a   Fusano, Akira ^a   Ryu, Ilhyong ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84879247785     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4011536     Document Type: Article

References (28)

1. Kharasch, M. S.; Skell, P. S.; Fisher, P. J. Am. Chem. Soc. 1948, 70, 1055
2. Kharasch, M. S.; Jensen, E. V.; Urry, W. H. Science 1945, 102, 128
3. Curran, D. P. Synthesis 1988, 489
4. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237
5. Byers, J. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, Chapter 1.5.
6. Pintauer, T.; Matyjaszewiski, K. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Chatgilialoglu, C.; Studer, A., Eds.; Wiley-VCH: Weinheim, 2012; Vol. 4, Chapter 62.
7. Curran, D. P.; Chen, M. H.; Spletzer, E.; Seong, C. M.; Chang, C. T. J. Am. Chem. Soc. 1989, 111, 8872
8. Curran, D. P.; Seong, C. M. J. Am. Chem. Soc. 1990, 112, 9401
9. Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746
10. Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1998, 1351
11. Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041
12. Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Org. Chem. 2001, 66, 7776
13. Renaud, P.; Ollivier, C.; Panchaud, P. Angew. Chem., Int. Ed. 2002, 41, 3460
14. Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755
15. Chabaud, L.; Landais, Y.; Renaud, P. Org. Lett. 2005, 7, 2587
16. Schär, P.; Renaud, P. Org. Lett. 2006, 8, 1569
17. Weidner, K.; Giroult, A.; Panchaud, P.; Renaud, P. J. Am. Chem. Soc. 2010, 132, 17511
18. Davies, T.; Haszeldine, R. N.; Tipping, A. E. J. Chem. Soc., Perkin Trans. 1 1980, 927
19. Tsuchii, K.; Imura, M.; Kamada, N.; Hirao, T.; Ogawa, A. J. Org. Chem. 2004, 69, 6658
20. Slodowicz, M.; Barata-Vallejo, S.; Vázquez, A.; Nudelman, N. S.; Postigo, A. J. Fluorine Chem. 2012, 135, 137
21. Kawamoto, T.; Fukuyama, T.; Ryu, I. J. Am. Chem. Soc. 2012, 134, 875
22. Ignatowska, J.; Dmowski, W. J. Fluorine Chem. 2006, 127, 720
23. Dmowski, W. J. Fluorine Chem. 2011, 132, 504
24. Matsubara, H.; Tsukida, M.; Ishihara, D.; Kuniyoshi, K.; Ryu, I. Synlett 2010, 2014
25. For bromine radical abstraction of hydrogen from the allylic position, see; Kharasch, M. S.; Schwartz, D.; Nudenberg, W. J. Org. Chem. 1953, 18, 337
26. Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L. J. Am. Chem. Soc. 2005, 127, 12513
27. Pozzi, D.; Scanlan, E. M.; Renaud, P. J. Am. Chem. Soc. 2005, 127, 14204
28. Povie, G.; Marzorati, M.; Bigler, P.; Renaud, P. J. Org. Chem. 2013, 78, 1553