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Synthesis and Application of Polystyrene Nanospheres Supported Platinum Catalysts in Enantioselective Hydrogenations

Catalysis Letters volume 141, pages 1435–1441 (2011)Cite this article

Abstract

Nearly monodisperse polystyrene nanospheres coated with platinum have been synthesized and applied successfully in the cinchona alkaloid-modified enantioselective hydrogenation of ethyl pyruvate. During the catalyst preparation broadly varied experimental conditions were used resulting in several catalysts with different properties. The effect of hydrogen pressure, solvent, modifier and polystyrene nanoparticle size on the enantioselectivity was also studied. Based on the results the effect of support on the mechanism of the enantiodifferentiation has been discussed.

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References

  1. Orito Y, Imai S, Niwa S (1979) J Chem Soc Jpn 8:1118

    Google Scholar 

  2. Orito Y, Imai S, Niwa S, Hung NG (1979) J Synth Org Chem Jpn 37:173

    Article  CAS  Google Scholar 

  3. Baiker A (2000) J Mol Catal A 163:205

    Article  CAS  Google Scholar 

  4. Huck WR, Bürgi T, Mallat T, Baiker A (2008) J Catal 216:276

    Article  Google Scholar 

  5. Tálas E, Margitfalvi JL (2008) Catal Commun 9:984

    Article  Google Scholar 

  6. Balázsik K, Cserényi S, Szöllösi G, Fülöp F, Bartók M (2008) Catal Lett 125:401

    Article  Google Scholar 

  7. Bartók M, Török B, Balázsik K, Bartók T (2001) Catal Lett 73:127

    Article  Google Scholar 

  8. Török B, Balázsik K, Felföldi K, Bartók M (2001) Ultrasonics Sonochem 8:191

    Article  Google Scholar 

  9. Garland M, Blaser HU (1990) J Am Chem Soc 112:7048

    Article  CAS  Google Scholar 

  10. Blaser HU, Garland M, Jalett HP (1993) J Catal 144:569

    Article  CAS  Google Scholar 

  11. Azyat K, Solladié-Cavallo A, Klein A, Welter R (2007) C R Chim 10:1180

    Article  CAS  Google Scholar 

  12. Solladié-Cavallo A, Marsol C, Azyat K, Roje M, Welch C, Chilenski J, Taillasson P, D’Orchymont H (2007) Eur J Org Chem 826

  13. Merlo AB, Ruggera JF, Santori GF, Moglioni A, Moltrasio Iglesias GY, Casella ML, Ferretti OA (2008) Catal Today 133–135:654

    Article  Google Scholar 

  14. Baiker A (1997) J Mol Catal A 115:473

    Article  CAS  Google Scholar 

  15. Schmidt E, Mallat T, Baiker A (2010) J Catal 272:140

    Article  CAS  Google Scholar 

  16. Pfaltz A, Heinz T (1997) Top Catal 4:229

    Article  Google Scholar 

  17. Blaser HU, Jalett HP, Lottenbach W, Studer M (2000) J Am Chem Soc 122:12675

    Article  CAS  Google Scholar 

  18. Simons KE, Meheux PA, Griffiths SP, Sutherland SP, Wells PB (1994) Recl Trav Chim Pays-Bas 113:465

    Article  CAS  Google Scholar 

  19. Blaser HU (2009) In: Song CE (ed) Cinchona alkaloids in synthesis and catalysis. Wiley-VCH, Weinheim, p 13

    Google Scholar 

  20. Sugimura T (2008) In: Ding K, Uozumi Y (eds) Handbook of asymmetric heterogeneous catalysis. WileyVCH, Weinheim, p 357

    Chapter  Google Scholar 

  21. Zaera F (2008) J Phys Chem C 112:16196

    Article  CAS  Google Scholar 

  22. Mallat T, Orglmeister E, Baiker A (2007) Chem Rev 107:4863

    Article  CAS  Google Scholar 

  23. Studer M, Blaser HU (2007) Acc Chem Res 40:1348

    Article  Google Scholar 

  24. Itsuno S, Haraguchi N (2008) In: Ding K, Uozumi Y (eds) Handbook of asymmetric heterogeneous catalysis. WileyVCH, Weinheim, p 73

    Chapter  Google Scholar 

  25. Thakur SS, Lee JE, Lee SH, Kim JM, Song CE (2008) In: Ding K, Uozumi Y (eds) Handbook of asymmetric heterogeneous catalysis. WileyVCH, Weinheim, p 27

    Google Scholar 

  26. Studer M, Blaser HU (2006) In: Ager D (ed) Handbook of chiral chemicals. CRC Press LLC, Boca Raton, p 345

    Google Scholar 

  27. Bartók M, Bartók T, Szöllösi G, Felföldi K (1999) Catal Lett 61:57

    Article  Google Scholar 

  28. Bartók M, Balázsik K, Szöllösi G, Bartók T (2000) J Catal 205:168

    Article  Google Scholar 

  29. Bhaduri S, Darshane VS, Sharma K, Mukesh D (1992) J Chem Soc, Chem Commun, 1738

  30. Zuo XB, Liu HF, Liu MH (1998) Tetrahedron Lett 39:1941

    Article  CAS  Google Scholar 

  31. Zuo XB, Liu HF, Guo DW, Yang XZ (1999) Tetrahedron 55:7787

    Article  CAS  Google Scholar 

  32. Bykov A, Matveeva V, Sulman M, Valetskiy P, Tkachenko O, Kustov L, Bronstein L, Sulman E (2009) Catal Today 140:64

    Article  CAS  Google Scholar 

  33. Borszeky K, Burgi T, Zhaohui Z, Mallat T, Baiker A (1999) J Catal 187:160

    Article  CAS  Google Scholar 

  34. Srikant P, Marci G, Raymond C, Prakash GKS (2000) Chem Mater 12:1985

    Article  Google Scholar 

Download references

Acknowledgments

Financial support provided by the ACS-Petroleum Research Fund, the University of Massachusetts Boston and Michigan Technological University is highly appreciated.

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Authors and Affiliations

  1. Department of Chemistry, University of Massachusetts Boston, Boston, MA, 02125, USA

    Béla Török, Aditya Kulkarni & Marianna Török

  2. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-1661, USA

    Ryan DeSousa & G. K. Surya Prakash

  3. Department of Chemistry, Michigan Technological University, Houghton, MI, 49931, USA

    Béla Török, Kalyani Satuluri & Marianna Török

Authors
  1. Béla Török
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  2. Aditya Kulkarni
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  3. Ryan DeSousa
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  4. Kalyani Satuluri
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  5. Marianna Török
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  6. G. K. Surya Prakash
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Correspondence to Béla Török.

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Török, B., Kulkarni, A., DeSousa, R. et al. Synthesis and Application of Polystyrene Nanospheres Supported Platinum Catalysts in Enantioselective Hydrogenations. Catal Lett 141, 1435–1441 (2011). https://doi.org/10.1007/s10562-011-0672-5

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  • DOI: https://doi.org/10.1007/s10562-011-0672-5

Keywords

  • Platinum
  • Polystyrene nanospheres
  • Cinchona alkaloids
  • Ethyl pyruvate
  • Hydrogenation
  • Enantioselective
  • Heterogeneous

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