Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Mild and Efficient Deoxygenation of Epoxides with Bis(cyclopentadienyl)titanium(IV) Dichloride-Indium System

  • Choi, Kwang-Hyun (Department of Advanced Materials Chemistry, Korea University) ;
  • Choi, Kyung-Il (Biochemicals Research Center, Korea Institute of Science and Technology) ;
  • Kim, Joong-Hyup (Biochemicals Research Center, Korea Institute of Science and Technology) ;
  • Yoon, Cheol-Min (Department of Advanced Materials Chemistry, Korea University) ;
  • Yoo, Byung-Woo (Department of Advanced Materials Chemistry, Korea University)
  • Published : 2005.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Kraus, G. A.; Thomas, P. J. J. Org. Chem. 1988, 53, 1395 https://doi.org/10.1021/jo00242a010
  2. Johnson, W. S.; Plummer, M. S.; Pulla Reddy, S.; Bartlett, W. R. J. Am. Chem. Soc. 1993, 115, 515 https://doi.org/10.1021/ja00055a022
  3. Mahesh, M.; Murphy, J. A.; Wessel, H. P. J. Org. Chem. 2005, 70, 4118 https://doi.org/10.1021/jo047904d
  4. Fujisawa, T.; Sugimoto, K.; Ohta, H. Chem. Lett. 1974, 883
  5. Santos, R. B.; Brocksom, T. J.; Brocksom, U. Tetrahedron Lett. 1997, 38, 745 https://doi.org/10.1016/S0040-4039(96)02451-3
  6. Patra, A.; Bandyopadhyay, M.; Dipakranjan, M. Tetrahedron Lett. 2003, 44, 2355 https://doi.org/10.1016/S0040-4039(03)00231-4
  7. Concellon, J. M.; Bardales, E. Org. Lett. 2002, 2, 189
  8. Schobert, R. Angew. Chem. Int. Ed. Engl. 1988, 27, 855 https://doi.org/10.1002/anie.198808551
  9. Martin, M. G.; Ganem, B. Tetrahedron Lett. 1984, 25, 251 https://doi.org/10.1016/S0040-4039(00)99853-8
  10. Coutts, R. S. P.; Wailes, P. C. J. Organomet. Chem. 1973, 47, 375 https://doi.org/10.1016/S0022-328X(00)81748-9
  11. Nelson, T. R.; Tufariello, J. J. J. Org. Chem. 1975, 40, 3159 https://doi.org/10.1021/jo00909a041
  12. Huang, Y.; Liao, P.; Zhang, Y. Synth. Commun. 1997, 27, 1059 https://doi.org/10.1080/00397919708003051
  13. McMurry, J. E. Chem. Rev. 1989, 89, 1513 https://doi.org/10.1021/cr00097a007
  14. Lenoir, D. Synthesis 1989, 883
  15. Furstner, A.; Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2442 https://doi.org/10.1002/anie.199624421
  16. Dushin, R. G. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 1071
  17. Yoo, B. W.; Choi, K. H.; Ko, J. J.; Nam, G. S.; Chang, K. Y.; Choi, K. I.; Kim, J. H. Bull. Korean Chem. Soc. 2001, 22, 541 https://doi.org/10.1007/BF02706639
  18. Yoo, B. W.; Choi, K. H.; Lee, S. J.; Yoon, C. M.; Kim, S. H.; Kim, J. H. Synth. Commun. 2002, 32, 63 https://doi.org/10.1081/SCC-120001509
  19. Yoo, B. W.; Lee, S. J.; Yoo, B. S.; Choi, K. I.; Kim, J. H. Synth. Commun. 2002, 32, 2489 https://doi.org/10.1081/SCC-120003398
  20. Yoo, B. W.; Choi, J. W.; Kim, D. Y.; Hwang, S. K.; Choi, K. I.; Kim, J. H. Bull. Korean Chem. Soc. 2002, 23, 797 https://doi.org/10.5012/bkcs.2002.23.6.797
  21. Mandal, A. K.; Mahajan, S. W. Tetrahedron 1988, 44, 2293 https://doi.org/10.1016/S0040-4020(01)81738-5
  22. Dos Santos, R. B.; Brocksom, T. J.; Brocksom, U. Tetrahedron Lett. 1997, 38, 745 https://doi.org/10.1016/S0040-4039(96)02451-3
  23. Martin, M. G.; Ganem, B. Tetrahedron Lett. 1984, 25, 251 https://doi.org/10.1016/S0040-4039(00)99853-8
  24. Gold, H. J. Synlett 1999, 159
  25. Fernandez-Mateos, A.; Martin de la Nava, E.; Pascual Coca, G.; Ramos Silvo, A.; Rubio Gonzales, R. Org. Lett. 1999, 1, 607 https://doi.org/10.1021/ol990699h
  26. McMurry, J. E.; Fleming, M. P. J. Org. Chem. 1975, 40, 2555 https://doi.org/10.1021/jo00905a040
  27. McMurry, J. E.; Silvestri, M. G.; Fleming, M. P.; Hoz, T.; Grayston, M. J. Org. Chem. 1978, 43, 3249 https://doi.org/10.1021/jo00411a001

Cited by

  1. Electrochemically Supported Deoxygenation of Epoxides into Alkenes in Aqueous Solution vol.14, pp.1, 2012, https://doi.org/10.1021/ol2026944
  2. A Facile and Efficient Reduction of Nitroarenes with NiCl2·6H2O/Indium System vol.27, pp.8, 2005, https://doi.org/10.5012/bkcs.2006.27.8.1115
  3. Mild and Efficient Deoxygenation of Epoxides with Bis(cyclopentadienyl)titanium(IV) Dichloride-Indium System. vol.37, pp.10, 2005, https://doi.org/10.1002/chin.200610063
  4. Mild and Efficient Deoxygenation of Amine‐N‐oxides with MoCl5/NaI System vol.38, pp.10, 2008, https://doi.org/10.1080/00397910801929739
  5. A Facile and Efficient Deoxygenation of Amine-N-oxides with WCl6/NaI System vol.29, pp.5, 2005, https://doi.org/10.5012/bkcs.2008.29.5.909
  6. Mild and Efficient Debromination of vic-Dibromides to Alkenes with NiCl2·6H2O/Indium System vol.29, pp.9, 2008, https://doi.org/10.5012/bkcs.2008.29.9.1655
  7. Mild and Efficient Deoxygenation of Amine-N-oxides with BiCl3/Indium System vol.39, pp.19, 2005, https://doi.org/10.1080/00397910902788190
  8. Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn vol.65, pp.15, 2005, https://doi.org/10.1016/j.tet.2009.02.013
  9. Rapid and Mild Deoxygenation of Sulfoxides with MoCl5/Gallium System under Ultrasonication vol.30, pp.9, 2005, https://doi.org/10.5012/bkcs.2009.30.9.1927
  10. Mixed disproportionation versus radical trapping in titanocene(III)-promoted epoxide openings vol.65, pp.52, 2005, https://doi.org/10.1016/j.tet.2009.10.038