Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Addition of α,α-Difluoroiodomethyl Ketones to Alkenes with a Copper Catalyst

  • Kwak, Kyung-Chell (Department of Bionanochemistry and Basic Sciences Research Institute, Wonkwang University) ;
  • Lee, Woo-Yiel (Department of Bionanochemistry and Basic Sciences Research Institute, Wonkwang University) ;
  • Zheshan, Quan (College of Pharmacy, Yanbian University) ;
  • Lee, Young-Hang (Department of Bionanochemistry and Basic Sciences Research Institute, Wonkwang University) ;
  • Yun, Young-Gab (Department of Prescription, School of Oriental Medicine, Wonkwang University) ;
  • Kwak, Gyu-Beum (Department of New Material Science, Chonbuk Natinoal University) ;
  • Chung, Hun-Taeg (Medicinal Resources Research Center of Wonkwang University) ;
  • Kwon, Tae-Oh (College of Life Science and Natural Resources, Wonkwang University) ;
  • Chai, Kyu-Yun (Department of Bionanochemistry and Basic Sciences Research Institute, Wonkwang University)
  • Published : 2005.01.20
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Abstract

The addition reactions of $\alpha$,$\alpha$-difluoroiodomethyl n-butyl ketone, α,α-difluoroiodomethyl cyclohexyl ketone, or $\alpha$,$\alpha$-difluoroiodomethyl phenyl ketone to alkenes were successfully accomplished in good yields in the presence of copper powder. The reaction was also applicable to alkenes containing a variety of functional groups such as ester, trimethylsilyl, or ether group. Acetonitrile was determined to be the best solvent in the present study and the reaction was performed at 55 ${^{\circ}C}$ for 15-22 h. This reaction provides a new, efficient and general method for the synthesis of $\alpha$,$\alpha$-difluoro functionalized ketones.

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References

  1. Filler, R.; Kobayashi, Y. Biochemical Aspects of Fluorine Chemistry; Elsevier Biochemical Press and Kodansha Ltd.: 1982; b) Filler, R. Biochemistry Involving Carbon-Fluorine Bonds; ACS: Washington D. C., 1976
  2. Welch, J. J. Tetrahedron 1987, 43, 3123 https://doi.org/10.1016/S0040-4020(01)90286-8
  3. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochem. 1985, 24, 1814 https://doi.org/10.1016/S0040-4020(01)90286-8
  4. Burkholder, C. R.; Dolbier, W. R.; Medebielle, M. J. Fluorine Chem. 2000, 102, 369 https://doi.org/10.1016/S0022-1139(99)00314-0
  5. Davis, C. R.; Burton, D. J.; Yang, Z. Y. J. Fluorine Chem. 1995, 70, 135 https://doi.org/10.1016/0022-1139(94)03102-6
  6. Elsheimer, S.; Dolbier, W. R.; Muria, M. J. Org. Chem. 1984, 49, 205 https://doi.org/10.1021/jo00175a054
  7. Rong, G.; Keese, R. Tetrahedron Lett. 1990, 31, 5615 https://doi.org/10.1016/S0040-4039(00)97911-5
  8. Huang, W. Y.; Wang, W.; Hung, B. N. Acta Chimical Sinia (Engl. Ed.) 1986, 178 https://doi.org/10.1016/S0040-4039(00)97911-5
  9. Hung, W. Y.; Zhang, H. J. J. Fluorine Chem. 1990, 50, 133 https://doi.org/10.1016/S0022-1139(00)82185-5
  10. Lang, R. W.; Schaud, B. Tetrahedron Lett. 1988, 29, 2943 https://doi.org/10.1016/0040-4039(88)85053-6
  11. Watanabe, S.; Fajita, T.; Sakamoto, M.; Takeda, H.; Kitazume, T.; Yamazaki, T. J. Fluorine Chem. 1997, 82, 1 https://doi.org/10.1016/S0022-1139(96)03535-X
  12. Qiu, Z.; Burton, D. J. J. Org. Chem. 1995, 60, 3465 https://doi.org/10.1021/jo00116a038
  13. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1991, 56, 170 https://doi.org/10.1021/jo00116a038
  14. Yang, Z. Y.; Burton, D. J. J. Fluorine Chem. 1989, 45, 435 https://doi.org/10.1016/S0022-1139(00)82877-8
  15. Chen, J.; Hu, C. M. J. Chem. Soc. Perkin Trans 1 1994, 1111 https://doi.org/10.1016/S0022-1139(00)82877-8
  16. Qiu, Z. M.; Burton, D. J. Tetrahedron Lett. 1994, 35, 1813 https://doi.org/10.1016/S0040-4039(00)73167-4
  17. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1992, 57, 5144 https://doi.org/10.1021/jo00045a027
  18. Qiu, Z. M.; Burton, D. J. Tetrahedron Lett. 1993, 34, 3239 https://doi.org/10.1016/S0040-4039(00)73671-9
  19. Kwak, K. C.; Oh, H. C.; Yun, Y. G.; Kim, B. H.; Lee, Y. H.; Chai, K. Y. Bull. Korrean Chem. Soc. 2002, 23(1), 157 https://doi.org/10.1016/S0040-4039(00)73671-9
  20. Kuroboshi, M.; Ishihara, T. Tetrahedron Lett. 1987, 28, 6481 https://doi.org/10.1016/S0040-4039(00)96894-1
  21. Kuroboshi, M.; Ishihara, T. Bull. Chem. Soc. Jpn. 1990, 63, 428 https://doi.org/10.1246/bcsj.63.428
  22. Chen, Q. Y.; Yang, Z. Y.; Zhao, C. X.; Qiu, Z. M. J. Chem. Soc. Perkin Trans 1 1998, 563 https://doi.org/10.1246/bcsj.63.428
  23. Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS: Washington, DC, 1991
  24. Yang, Z. Y.; Burton, D. J. Tetrahedron Lett. 1991, 32, 1019 https://doi.org/10.1016/S0040-4039(00)74476-5
  25. Kitagawa, O.; Miura, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1011 https://doi.org/10.1016/S0040-4039(00)74476-5
  26. Kitagawa, O.; Miura, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1011
  27. Chem. Lett. Kitagawa, O.; Miura,A.; Kobayashi, Y.; Taguchi, T.

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