Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Carboxylation of Styrene Oxide Catalyzed by Quaternary Onium Salts under Solvent-free Conditions

  • Shim, Jae-Jin (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Kim, Duck (Department of Chemistry and Institute of Natural Science, Yeungnam University) ;
  • Ra, Choon-Sup (Department of Chemistry and Institute of Natural Science, Yeungnam University)
  • Published : 2006.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Trost, B. M. Science 1991, 254, 1471 https://doi.org/10.1126/science.1962206
  2. Trost, B. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 259 https://doi.org/10.1002/anie.199502591
  3. Trost, B. M. Angew. Chem.Int. Ed. Engl. 1995, 34, 281
  4. Sheldon, R. A. Chem. Ind. 1992, 903
  5. Darensbourg, D. J.; Holtcamp, M. W. Coord. Chem. Rev. 1996, 153, 155 https://doi.org/10.1016/0010-8545(95)01232-X
  6. Shaikh, A. A. G.; Sivaram, S. Chem. Rev. 1996, 96, 951 https://doi.org/10.1021/cr950067i
  7. Nicolaou, K. C.; Couladouros, E. A.; Nantermet, P. G.; Renaud,J.; Guy, R. K.; Wrasidlo, W. Angew. Chem., Int. Ed. Engl. 1994, 33, 1581 https://doi.org/10.1002/anie.199415811
  8. Clements, J. H. Ind. Eng. Chem. Res. 2003, 42, 663 https://doi.org/10.1021/ie020678i
  9. Beckman, E. J. Ind. Eng. Chem. Res. 2003, 42, 1598 https://doi.org/10.1021/ie0300530
  10. Behr, A. Carbon Dioxide Activation by Metal Complexes;VCH: Weinheim, Germany, 1988; pp 91-93
  11. McMullen, C. H.;Nelson, J. R.; Ream, B. C.; Sims, J. A., Jr. Alkylene CarbonateProcess. U.S. Patent 4,314,945, Feb. 9, 1982
  12. Shen, Y.-M.; Duan, W.-L.; Shi, M. J. Org. Chem. 2003, 68, 1559 https://doi.org/10.1021/jo020191j
  13. Yamaguchi, K.; Ebitani, K.; Yoshida,T.; Yoshida, H.; Kaneda, K. J. Am. Chem. Soc. 1999, 121, 4526 https://doi.org/10.1021/ja9902165
  14. Kim, H. S.; Kim, J. J.; Lee, B. G.; Jung, O. S.; Jang, H. G.;Kang, S. O. Angew. Chem. Int. Ed. 2000, 39, 4096 https://doi.org/10.1002/1521-3773(20001117)39:22<4096::AID-ANIE4096>3.0.CO;2-9
  15. Darensbourg, D. J.; Wildeson, J. R.; Yarbrough, J. C.;Reibenspies, J. H. J. Am. Chem. Soc. 2000, 122, 12487 https://doi.org/10.1021/ja002855h
  16. Allen,S. D.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 14284 https://doi.org/10.1021/ja028071g
  17. Kim, H. S.; Kim, J. J.; Kwon, H.N.; Chung, M. J.; Lee, B. G.; Jang, H. G. J. Catal. 2002, 205, 226 https://doi.org/10.1006/jcat.2001.3444
  18. Calo, V.; Nacci, A.; Monopoli, A.; Fanizzi, A.Org. Lett. 2002, 4, 2561 https://doi.org/10.1021/ol026189w
  19. Huang, J.-W.; Shi, M. J. Org. Chem. 2003, 68, 6705 https://doi.org/10.1021/jo0348221
  20. Kim, H. S.; Kim, J. J.; Lee, S. D.; Lah, M. S.; Moon, D.; Jang,H. G. Chem. Eur. J. 2003, 9, 678 https://doi.org/10.1002/chem.200390076
  21. Kawanami, H.; Sasaki, A.;Matsui, K.; Ikushima, Y. Chem. Commun. 2003, 896
  22. Kim, Y.-J.; Cheong, M.Bull. Korean Chem. Soc.2002, 23, 1027 https://doi.org/10.5012/bkcs.2002.23.7.1027
  23. Matzuda, H.; Niangawa, A.; Nomura, R. Chem. Lett. 1979,1261
  24. Nomura, R.; Ninagawa, A.; Matsuda, H. J. Org. Chem.1980, 45, 3735 https://doi.org/10.1021/jo01307a002
  25. Kisch, H.; Millini, R.; Wang, I. J. Chem. Ber. 1986, 119, 1090 https://doi.org/10.1002/cber.19861190329
  26. Duemler, W.; Kisch, H. Chem. Ber. 1990, 123, 277 https://doi.org/10.1002/cber.19901230209
  27. Li, F.; Xia, C.; Xu, L.; Chen, G. Chem. Comm.2003, 2042
  28. Lu, X.-B.; Liang, B.; Zhang, Y.-Z.; Wang, Y.-M.; Bai,C.-X.; Wang, H.; Zhang, R. J. Am. Chem. Soc. 2004, 126, 3732 https://doi.org/10.1021/ja049734s
  29. Kawanami, H.; Sasaki, A.; Matsui, K.; Ikushima, Y. Chem.Comm.2003, 896
  30. Huang, J.-W.; Shi, M. J. Org. Chem.2003, 68, 6705 https://doi.org/10.1021/jo0348221

Cited by

  1. Insights into quaternary ammonium salts-catalyzed fixation carbon dioxide with epoxides vol.2, pp.7, 2012, https://doi.org/10.1039/c2cy20103h
  2. Efficient Ring Opening Reaction of Epoxides with Oxygen Nucleophiles Catalyzed by Quaternary Onium Salt vol.34, pp.8, 2013, https://doi.org/10.5012/bkcs.2013.34.8.2286
  3. /Phosphine-Catalyzed Coupling Reactions of Carbon Dioxide and Epoxides vol.5, pp.6, 2013, https://doi.org/10.1002/cctc.201200770
  4. Phosphorus-based Bifunctional Organocatalysts for the Addition of Carbon Dioxide and Epoxides vol.7, pp.12, 2014, https://doi.org/10.1002/cssc.201402477
  5. Bifunctional One-Component Catalysts for the Addition of Carbon Dioxide to Epoxides vol.7, pp.3, 2015, https://doi.org/10.1002/cctc.201402816
  6. vol.5, pp.11, 2015, https://doi.org/10.1021/acscatal.5b01545
  7. Atom economical synthesis of di- and trithiocarbonates by the lithium tert-butoxide catalyzed addition of carbon disulfide to epoxides and thiiranes vol.14, pp.31, 2016, https://doi.org/10.1039/C6OB01081D
  8. One-Pot Synthesis of Styrene Carbonate from Styrene and CO2 Over the Nanogold-Ionic Liquid Catalyst vol.146, pp.5, 2016, https://doi.org/10.1007/s10562-016-1703-z
  9. Tetraarylphosphonium Salt-Catalyzed Carbon Dioxide Fixation at Atmospheric Pressure for the Synthesis of Cyclic Carbonates vol.6, pp.10, 2016, https://doi.org/10.1021/acscatal.6b02265
  10. Carbon Dioxide Oversolubility in Nanoconfined Liquids for the Synthesis of Cyclic Carbonates vol.9, pp.11, 2017, https://doi.org/10.1002/cctc.201700247
  11. Carboxylation of Styrene Oxide Catalyzed by Quaternary Onium Salts under Solvent-Free Conditions. vol.37, pp.51, 2006, https://doi.org/10.1002/chin.200651091
  12. Phosphonium Salt Organocatalysis vol.351, pp.10, 2009, https://doi.org/10.1002/adsc.200900211
  13. Harnessing CO2 into Carbonates Using Heterogeneous Waste Derivative Cellulose-Based Poly(ionic liquids) as Catalysts vol.149, pp.3, 2019, https://doi.org/10.1007/s10562-018-2637-4
  14. Solvent-free Carboxylation of Styrene Oxide: Enhanced Reactivity of Quaternary Onium Salts in Ionic Liquid-CO2 System vol.28, pp.6, 2007, https://doi.org/10.5012/bkcs.2007.28.6.1060
  15. Cyclic Carbonate Synthesis Catalysed by Bimetallic Aluminium–Salen Complexes vol.16, pp.23, 2006, https://doi.org/10.1002/chem.201000030
  16. Synthesis of Cyclic Carbonates from Epoxides and Carbon Dioxide by Using Bifunctional One-Component Phosphorus-Based Organocatalysts vol.8, pp.16, 2006, https://doi.org/10.1002/cssc.201500612
  17. Iron(III) Versatile Catalysts for Cycloaddition of CO2 to Epoxides and Epoxidation of Alkenes vol.1, pp.9, 2006, https://doi.org/10.1002/slct.201600488
  18. Recent Developments in the Synthesis of Cyclic Carbonates from Epoxides and CO2 vol.375, pp.3, 2017, https://doi.org/10.1007/s41061-017-0136-5
  19. Mechanistic Study on the Addition of CO2 to Epoxides Catalyzed by Ammonium and Phosphonium Salts: A Combined Spectroscopic and Kinetic Approach vol.6, pp.8, 2006, https://doi.org/10.1021/acssuschemeng.8b02093
  20. Sequential Selective C−H and C(sp3)−+P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds vol.133, pp.50, 2006, https://doi.org/10.1002/ange.202111164
  21. Sequential Selective C−H and C(sp3)−+P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds vol.60, pp.50, 2006, https://doi.org/10.1002/anie.202111164