Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of 2-Phenylated 1,1-difluoro-1,3-enynes via Alkynylation of β,β-Difluoro-α-phenylvinylstannane

  • Han, Seung-Yeon (Department of Chemistry and Medical Chemistry, Yonsei University) ;
  • Choi, Ji-Hoon (Department of Chemistry and Medical Chemistry, Yonsei University) ;
  • Hwang, Ji-Hye (Department of Chemistry and Medical Chemistry, Yonsei University) ;
  • Jeong, In-Howa (Department of Chemistry and Medical Chemistry, Yonsei University)
  • Received : 2010.03.11
  • Accepted : 2010.03.15
  • Published : 2010.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Mikaelin, G. S.; Gybin, A. S.; Smit, W. A.; Caple, R. Tetrahedron Lett. 1985, 26, 1269. https://doi.org/10.1016/S0040-4039(00)94867-6
  2. Zweifel, G.; Rajagopalan, S. J. Am. Chem. Soc. 1985, 107, 700. https://doi.org/10.1021/ja00289a029
  3. Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687. https://doi.org/10.1021/jo990847h
  4. Gabriele, B.; Salerno, G.; Fazio, A. Org. Lett. 2000, 2, 351. https://doi.org/10.1021/ol991297c
  5. Gabriele, B.; Salerno, G.; Fazio, A. J. Org. Chem. 2003, 68, 7853. https://doi.org/10.1021/jo034850j
  6. Normant, J. F.; Commercon, A.; Villieras, J. Tetrahedron Lett. 1975, 16, 1465. https://doi.org/10.1016/S0040-4039(00)72170-8
  7. Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. https://doi.org/10.1021/ol030010f
  8. Shi, J.; Zeng, X.; Negishi, E. Org. Lett. 2003, 5, 1825. https://doi.org/10.1021/ol030017x
  9. Xu, Z.-Q.; Zamlicka, J. Tetrahedron 1997, 53, 5389. https://doi.org/10.1016/S0040-4020(97)00233-0
  10. Eddarir, S.; Francesch, C.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1997, 8-9, 741.
  11. Saito, S.; Kawasaki, T.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 2001, 66, 796. https://doi.org/10.1021/jo0056242
  12. Wang, Y.; Xu, J.; Burton, D. J. J. Org. Chem. 2006, 71, 7780. https://doi.org/10.1021/jo061305k
  13. Silveira, C. C.; Braga, A. L.; Vieira, A. S.; Zeni, G. J. Org. Chem. 2003, 68, 662 https://doi.org/10.1021/jo0261707
  14. Yang, Z.-Y.; Burton, D. J. Tetrahedron Lett. 1990, 31, 1369. https://doi.org/10.1016/S0040-4039(00)88808-5
  15. Yang, Z.-Y.; Burton, D. J. J. Fluorine Chem. 1991, 53, 307. https://doi.org/10.1016/S0022-1139(00)80956-2
  16. Eddarir, S.; Francesch, C.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1990, 31, 4449. https://doi.org/10.1016/S0040-4039(00)97645-7
  17. Eddarir, S.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1991, 32, 69. https://doi.org/10.1016/S0040-4039(00)71220-2
  18. Percy, J.; Wilkes, R. D. Tetrahedron 1997, 53, 14749. https://doi.org/10.1016/S0040-4020(97)00986-1
  19. Yoshida, M.; Yoshikawa, S.; Fukuhara, T.; Yoneda, N.; Hara, S. Tetrahedron 2001, 57, 7143. https://doi.org/10.1016/S0040-4020(01)00683-4
  20. Mei, Y.-Q.; Liu, J.-T. Tetrahedron 2008, 64, 8801. https://doi.org/10.1016/j.tet.2008.06.084
  21. Yoshida, M.; Komata, A.; Hara, S. Tetrahedron 2006, 62, 8636. https://doi.org/10.1016/j.tet.2006.05.085
  22. Zapata, A. J.; Gu, Y.; Hammond, G. B. J. Org. Chem. 2000, 65, 227. https://doi.org/10.1021/jo991620p
  23. Burton, D. J.; Lee, T. M. J. Fluorine Chem. 1976, 8, 189. https://doi.org/10.1016/S0022-1139(00)82696-2
  24. Tellier, F.; Sauvetre, R.; Normant, J.-F. Tetrahedron Lett. 1986, 27, 3147. https://doi.org/10.1016/S0040-4039(00)84738-3
  25. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281. https://doi.org/10.1016/S0022-1139(00)80572-2
  26. Choi, J. H.; Jeong, I. H. Tetrahedron Lett. 2008, 49, 952. https://doi.org/10.1016/j.tetlet.2007.12.028
  27. Damle, S. V.; Seomoon, D.; Lee, P. H. J. Org. Chem. 2003, 68, 7085. https://doi.org/10.1021/jo034727s

Cited by

  1. Preparation of 2,2-Difluoro-1-arylethenylstannane as a Precursor of 1,1-Diaryl-2,2-difluoroethenes vol.33, pp.2, 2012, https://doi.org/10.5012/bkcs.2012.33.2.379
  2. -Tosylhydrazones: Access to 1,1-Difluoro-1,3-enynes vol.17, pp.10, 2015, https://doi.org/10.1021/acs.orglett.5b00980
  3. The Synthesis and Characterization of Some Novel Thioethers: Thio-Subsituted [3]Cumulenes, -1-Buten-3-ynes and Buta-1,3-dienes vol.31, pp.8, 2010, https://doi.org/10.5012/bkcs.2010.31.8.2255