Bulletin of the Korean Chemical Society

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Tin-free Radical Acylation Reactions Using Alkyl Allyl Sulfones as Radical Precursors

  • Kim, Sung-Gak (Center for Molecular Design & Synthesis and Department of Chemistry,School of Molecular Science, Korea Advanced Institute of Science and Technology) ;
  • Lim, Chae-Jo (Center for Molecular Design & Synthesis and Department of Chemistry,School of Molecular Science, Korea Advanced Institute of Science and Technology)
  • Published : 2003.08.20
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References

  1. Baguley, P. A.; Walton, J. C. Angew. Chem. Int. Ed. 1998, 37,3072. https://doi.org/10.1002/(SICI)1521-3773(19981204)37:22<3072::AID-ANIE3072>3.0.CO;2-9
  2. Curran, D. P.; Haida, S. J. Am. Chem. Soc. 1996, 118, 2531. https://doi.org/10.1021/ja953287m
  3. Curran, D. P.; Haida, S.; Kim, S.-Y.; Luo, Z. J. Am. Chem. Soc.1999, 121, 6607. https://doi.org/10.1021/ja990069a
  4. Gerigke, U.; Gerlach, M.; Neumann, W. P.; Vieler, R.;Weintritt, V. Synthesis 1990, 448.
  5. Gerlach, M.; Jordens, F.;Kuhn, H.; Neumann, W. P.; Peterseim, M. J. Org. Chem. 1991,56, 5971. https://doi.org/10.1021/jo00021a001
  6. Dumartin, G.; Ruel, G.; Kharboutli, J.; Delmond, B.; Connil, M.-F.; Jousseaume, B.; Pereyre, M. Synlett 1994,952.
  7. Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1988,53, 3641. https://doi.org/10.1021/jo00250a051
  8. Giese, B.; Kopping, B.; Chatgilialoglu, C. TetrahedronLett. 1989, 30, 681. https://doi.org/10.1016/S0040-4039(01)80281-1
  9. Ballestri, M.; Chatgilialoglu, C. J. Org.Chem. 1991, 56, 678. https://doi.org/10.1021/jo00002a035
  10. Chatgilialoglu, C. Acc. Chem. Res. 1992,25, 188. https://doi.org/10.1021/ar00016a003
  11. Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229. https://doi.org/10.1021/cr00037a005
  12. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1229.
  13. Zard, S.Z. Angew. Chem. Int. Ed. 1997, 36, 672. https://doi.org/10.1002/anie.199706721
  14. Bertrand, M. Org.Prep. Proced. Int. 1994, 26, 257. https://doi.org/10.1080/00304949409458426
  15. Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118,1209. https://doi.org/10.1021/ja9522443
  16. Guyader, F. L.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z.J. Am. Chem. Soc. 1997, 119, 7410. https://doi.org/10.1021/ja9708878
  17. Quiclet-Sire, B.; Seguin,S.; Zard, S. Z. Angew. Chem. Int. Ed. 1998, 37, 2864. https://doi.org/10.1002/(SICI)1521-3773(19981102)37:20<2864::AID-ANIE2864>3.0.CO;2-W
  18. Bertrand,F.; Guyader, F. L.; Liguori, L.; Ouvry, G.; Quiclet-Sire, B.; Seguin,S.; Zard, S. Z. C. R. Acad. Sci. Paris, Chimie 2001, 4, 547.
  19. Bertrand, F.; Quiclet-Sire, B.; Zard, S. Z. Angew. Chem. Int.Ed. 1999, 38, 1943. https://doi.org/10.1002/(SICI)1521-3773(19990712)38:13/14<1943::AID-ANIE1943>3.0.CO;2-R
  20. Xiang, J.; Jiang, W.; Gong, J.; Fuchs, P. L.J. Am. Chem. Soc. 1997, 119, 4123. https://doi.org/10.1021/ja963636s
  21. Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2000, 122, 6496. https://doi.org/10.1021/ja000673h
  22. Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2001, 123, 4717. https://doi.org/10.1021/ja004129k
  23. Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc.1996, 118, 5138. https://doi.org/10.1021/ja9600993
  24. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997,119, 5982. https://doi.org/10.1021/ja9710316
  25. Kim, S.; Song, H.-J.; Choi, T.-L.; Yoon, J.-Y. Angew. Chem. Int.Ed. 2001, 40, 2524. https://doi.org/10.1002/1521-3773(20010702)40:13<2524::AID-ANIE2524>3.0.CO;2-4
  26. Kim, S.; Lim, C. J. Angew. Chem. Int. Ed. 2002, 41, 3265. https://doi.org/10.1002/1521-3773(20020902)41:17<3265::AID-ANIE3265>3.0.CO;2-X
  27. Forbes, J. E.; Zard, S. Z. J. Am. Chem. Soc. 1990, 112, 2034. https://doi.org/10.1021/ja00161a078
  28. Kim, S.; Lee, I. Y. Tetrahedron Lett. 1998, 39, 1587. https://doi.org/10.1016/S0040-4039(98)00035-5
  29. Curran, D. P.; van Elburg, P. A.; Giese, B.; Giles, S. TetrahedronLett. 1990, 31, 2861. https://doi.org/10.1016/0040-4039(90)80167-K

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