DOI QR코드

DOI QR Code

Synthesis of New Bimetallic Chiral Salen Catalyst Bearing Co(BF4)2 Salt and Its Application in Asymmetric Ring Opening of Epoxide

  • Kim, Yong-Suk (Department of Chemical Engineering, Inha University) ;
  • Lee, Choong-Young (Department of Chemical Environmental Technology, Inha Technical College) ;
  • Kim, Geon-Joong (Department of Chemical Engineering, Inha University)
  • Received : 2010.04.08
  • Accepted : 2010.09.03
  • Published : 2010.10.20

Abstract

The newly synthesized homogeneous chiral Co(III) salen complexes were anchored non-covalently on the acidic sites of mesoporous Al-SBA-15. The Bronsted and Lewis acidic sites are attributed to the immobilization of fluorine functionalized chiral salen complexes on the supports. XRD, BET, TEM, FT-IR and ESCA (XPS) analyses were performed to characterize the property of support, and the structure of new homogeneous and heterogeneous chiral Co salen catalyst. The homogeneous and heterogeneous catalysts could be applied in asymmetric ring opening of epichlorohydrine (ECH) by water. They showed very high enantioselectivity and a good yield up to 99% in the catalytic synthesis of optically active products.

Keywords

References

  1. Karlsson, A.; Stocker, M.; Schmidt, R. Micropor. Mesopor. Mater. 1999, 27, 181. https://doi.org/10.1016/S1387-1811(98)00252-2
  2. Demel, J.; Park, S.-E.; Cejka, J.; Stepnicka, P. Catal. Today. 2008, 132, 63. https://doi.org/10.1016/j.cattod.2007.12.007
  3. Nur, H.; Hamid, H.; Endud, S.; Hamdan, H.; Ramli, Z. Mater. Chem. Phys. 2006, 96, 337. https://doi.org/10.1016/j.matchemphys.2005.07.023
  4. Kim, J. M.; Kwak, J. H.; Jun, S.; Ryoo, R. J. Phys. Chem. 1995, 99, 16742. https://doi.org/10.1021/j100045a039
  5. Yang, H.; Li, J.; Yang, J.; Liu, Z.; Yang, Q.; Li, C. Chem. Commun. 2007, 1086.
  6. Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710. https://doi.org/10.1002/hlca.19960790621
  7. Vasylev, M. V.; Neumann, R. J. Am. Chem. Soc. 2004, 126, 126.
  8. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. https://doi.org/10.1126/science.277.5328.936
  9. Kawthekar, R. B.; Kim, G.-J. Helvetica Chimica Acta 2008, 91, 317. https://doi.org/10.1002/hlca.200890037
  10. Kawthekar, R. B.; Bi, W. T.; Kim, G.-J. Appl. Organometal. Chem. 2008, 22, 583. https://doi.org/10.1002/aoc.1447
  11. Kawthekar, R. B.; Bi, W. T.; Kim, G.-J. Bull. Korean Chem. Soc. 2008, 29, 313. https://doi.org/10.5012/bkcs.2008.29.2.313
  12. Kim, Y. S.; Lee, C.-Y.; Kim, G.-J. Bull. Korean Chem. Soc. 2009, 30, 1771. https://doi.org/10.5012/bkcs.2009.30.8.1771
  13. Lee, K.-W.; Lee, C.-Y.; Kim, G.-J. Bull. Korean Chem. Soc. 2009, 30, 389. https://doi.org/10.5012/bkcs.2009.30.2.389
  14. Kim, Y. S.; Guo X. F.; Kim, G.-J. Catalysis Today 2010, 150, 91. https://doi.org/10.1016/j.cattod.2009.09.005
  15. Gan, J.; Wang, T.; Liu, Z.; Tan, W. Stud. Surf. Sci. Catal. 2007, 170B, 1567.

Cited by

  1. ChemInform Abstract: Synthesis of New Bimetallic Chiral Salen Catalyst Bearing Co(BF4)2 Salt and Its Application in Asymmetric Ring Opening of Epoxide. vol.42, pp.10, 2011, https://doi.org/10.1002/chin.201110099
  2. Enantioselective Cobalt-Catalyzed Transformations vol.114, pp.5, 2014, https://doi.org/10.1021/cr4004055
  3. Application of Mesoporous Silica Foam for Immobilization of Salen Complexes in Chiral Intermediates Synthesis vol.36, pp.5, 2015, https://doi.org/10.1002/bkcs.10271
  4. : enhanced enantioselectivity in the hydrolytic kinetic resolution of epoxides vol.5, pp.101, 2015, https://doi.org/10.1039/C5RA12408E
  5. Microporous organic networks bearing metal-salen species for mild CO2 fixation to cyclic carbonates vol.1, pp.18, 2013, https://doi.org/10.1039/c3ta10477j
  6. Asymmetric Ring-Opening of Epoxides Catalyzed by Metal-Salen Complexes vol.10, pp.6, 2010, https://doi.org/10.3390/catal10060705