DOI QR코드

DOI QR Code

Rapid and Efficient Debromination of vic-Dibromides with VCl3/Indium System

Yoo, Byung Woo;Park, Jee Yeon;Shin, Hyo Jong

  • 투고 : 2018.02.28
  • 심사 : 2018.05.14
  • 발행 : 2018.08.20

초록

The $VCl_3$/In system was found to be a new protocol for debromination of a variety of vic-dibromides to the corresponding alkenes in high yields with short reaction times under mild conditions. This new methodology is highly chemoselective, tolerating several functional groups such as chloro, bromo, fluoro, keto, ester, carboxyl, and methoxy groups.

키워드

Debromination;vic-Dibromide;Vanadium(III) chloride;Indium

참고문헌

  1. (b) Li, C. J.; Harpp, D. N. Tetrahedron Lett. 1990, 31, 6291. https://doi.org/10.1016/S0040-4039(00)97045-X
  2. (c) Malanga, C.; Mannucci, S.; Lardicci, L. Tetrahedron 1998, 54, 1021. https://doi.org/10.1016/S0040-4020(97)10203-4
  3. (d) Tanata, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett. 1996, 37, 9313. https://doi.org/10.1016/S0040-4039(97)82951-6
  4. (e) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. J. Chem. Soc. Chem. Commun. 1998, 2113.
  5. (f) Ranu, B. C.; Jana, K.; Miller, R. J. Org. Chem. 2005, 70, 8621. https://doi.org/10.1021/jo051373r
  6. (g) Ranu, B. C.; Das, A.; Hajra, A. Synthesis 2003, 1012.
  7. (h) Xu, X.; Zhang, Y. Synth. Commun. 2000, 30, 1917. https://doi.org/10.1080/00397910008087241
  8. (b) Hirao, T.; Asahara, M.; Muguruma, Y.; Ogawa, A. J. Org. Chem. 1998, 63, 2812. https://doi.org/10.1021/jo980376j
  9. (c) Hirao, T.; Hatano, B.; Ima- moto, Y.; Ogawa, A. J. Org. Chem. 1999, 64, 7665. https://doi.org/10.1021/jo990902m
  10. (d) Takahara, P. M.; Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. Tetrahedron Lett. 1989, 30, 7177. https://doi.org/10.1016/S0040-4039(01)93927-9
  11. (e) Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014. https://doi.org/10.1021/ja00202a053
  12. (b) Cintas, P. Synlett 1995, 1087.
  13. (c) Auge, J.; Lubin-Germain, N.; Uziel, J. Synthesis 2007, 1739.
  14. (d) Li, C. J. Tetrahedron 1996, 52, 5643. https://doi.org/10.1016/0040-4020(95)01056-4
  15. (e) Pitts, M. R.; Harrison, J. R.; Moody, C. J. J. Chem. Soc, Perkin Trans. I 2001, 955.
  16. (b) Yoo, B. W.; Park, M. C.; Shin, J. I. Bull. Korean Chem. Soc. 2009, 30, 1927. https://doi.org/10.5012/bkcs.2009.30.9.1927
  17. (c) Yoo, B. W.; Min, S. K. Synth. Commun. 2011, 41, 2993. https://doi.org/10.1080/00397911.2010.516382
  18. (d) Yoo, B. W.; Kim, D. I.; Kim, H. M.; Kim, S. H. Bull. Korean Chem. Soc. 2012, 33, 2851. https://doi.org/10.5012/bkcs.2012.33.9.2851
  19. (e) Yoo, B. W.; Kim, S. H.; Min, G. H. Bull. Korean Chem. Soc. 2012, 33, 27. https://doi.org/10.5012/bkcs.2012.33.1.27
  20. (f) Yoo, B. W.; Lee, S. J.; Park, Y. K.; Choi, J. Y.; Ahn, Y. S. Bull. Korean Chem. Soc. 2013, 34, 1951.
  21. (b) Khurana, J. M.; Gogia, A.; Bankhwal, R. K. Synth. Commun. 1997, 27, 1801. https://doi.org/10.1080/00397919708004093
  22. (c) Yanada, R.; Bessho. K.; Yanada, K. Synlett 1995, 443.
  23. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd ed.; New York, 1991.
  24. (a) Buther, T. S.; Detty, M. R. J. Org. Chem. 1998, 63, 169. https://doi.org/10.1021/jo9713363
  25. (a) Raw A. S.; Pedersen, S. F. J. Org. Chem. 1991, 56, 830. https://doi.org/10.1021/jo00002a059
  26. Hirao, T.; Hirano, K.; Hasegawa, T.; Ohshiro, Y.; Ikeda, I. J. Org. Chem. 1993, 58, 6529. https://doi.org/10.1021/jo00075a070
  27. (a) Nair, V.; Ros, S.; Jayan, C. N.; Pillia, B. S. Tetrahedron 2004, 60, 1959. https://doi.org/10.1016/j.tet.2003.12.037
  28. Podlech, J.; Maier, T. C. Synthesis 2003, 633.
  29. (a) Yoo, B. W.; Song, M. S.; Park, M. C. Synth. Commun. 2007, 37, 3089. https://doi.org/10.1080/00397910701544729
  30. (a) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. Tetrahedron Lett. 1987, 28, 5287. https://doi.org/10.1016/S0040-4039(00)96709-1

과제정보

연구 과제 주관 기관 : Korea University