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Oxidation of α-methylstyrene on an MCM-22 encapsulated (R, R)-(−)-N, N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) catalyst

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Central European Journal of Chemistry

Abstract

(R, R)-(−)-N, N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) was encapsulated into MCM-22 using the zeolite synthesis method. The encapsulated catalyst proved to be active in the oxidation of α-methylstyrene with NaOCl with higher specific activity than the homogeneous catalyst. At the same time, this encapsulated catalyst was completely inactive in the hydrolytic kinetic resolution of racemic styrene oxide. This observation is in a good correlation with the assumption of the cooperative bimetallic mechanism proposed by Annis and Jacobsen.

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References

  1. D.E. De Vos, I.F.J. Vankelecom and P.A. Jacobs: Chiral Catalyst Immobilization and Recycling, Wiley-VCH, Weinheim, 2000.

    Google Scholar 

  2. D.E. De Vos, M. Dams, B.F. Sels and P.A. Jacobs: “Ordered Mesoporous and Microporous Molecular Sieves Functionalized with Transition Metal Complexes as Catalysts for Selective Organic Transformations”, Chem. Rev., Vol. 102, (2002), pp. 3615–3640.

    Article  CAS  Google Scholar 

  3. C. Bianchini and P. Barbaro: “Recent aspects of asymmetric catalysis by immobilized chiral metal catalysts”, Topics Catal., Vol. 19, (2002), pp. 17–32.

    Article  CAS  Google Scholar 

  4. M.J. Sabater, A. Corma, A. Domenech, V. Fornes and H. Garcia: “Chiral salen maganese complex encapsulated within zeolite Y: a heterogeneous enantioselective catalyst for the epoxidation of alkenes”, J. Chem. Soc., Chem. Commun., (1997), pp. 1285–1286.

  5. S.B. Ogunwumi and T. Bein: “Intrazeolite assembly of a chiral manganese salen expoxidation catalysts”, J. Chem. Soc., Chem. Commun., (1997), pp. 901–902.

  6. C. Reyes, Y. Gao, Á. Zsigmond, P. Goel, N. Mahata, S. Tanielyan and R.L. Augustine: “Solvent Effects in the Use of Anchored Homogeneous Catalyst for Hydrogenation Reactions”, Chemistry Industry (Dekker), Vol. 89, (2002), pp. 627–632.

    Google Scholar 

  7. R.L. Augustine, S.K. Tanielyan, N. Mahata, Y Gao, Á. Zsigmond and H. Yang: “Anchored homogeneous catalysts: The role of the heteropoly acid anchoring agent”, Appl. Catal. A-General, Vol. 256, (2003), pp. 69–76.

    Article  CAS  Google Scholar 

  8. Á. Zsigmond, K. Bogár and F. Notheisz: “Comparative study of “Ship-in-a-bottle” and Anchored Rh Complexes”, J. Catal., Vol. 213, (2003), pp. 103–108.

    Article  CAS  Google Scholar 

  9. M. E. Leonowicz, J.A. Lawton and M.K. Rubin: “MCM-22—a molecular sieve with two independent multidimensional channel systems”, Science, Vol. 264, (1994), pp. 1910–1913.

    Article  CAS  Google Scholar 

  10. G. Gbery, Á. Zsigmond and D.J. Balkus, Jr.: “Enantioselective epoxidations catalyzed by zeolite MCM-22 encapsulated Jacobsen’s catalyst”, Catal. Lett., Vol. 74, (2001), pp. 77–80.

    Article  CAS  Google Scholar 

  11. Á. Zsigmond, F. Notheisz, Z. Fráter and J.E. Bäckvall: “Selective oxidation of alcohols on zeolite encapsulated cobalt salophen catalysts”, Studies in Surface Science and Catalysis, Vol. 108, (1997), pp. 453–459.

    CAS  Google Scholar 

  12. Á. Zsigmond, F. Notheisz, G. Csjernyik and J.E. Bäckvall: “Ruthenium-catalyzed aerobic oxidation of alcohols on zeolite-encapsulated cobalt salophen catalyst”, Top. Catal., Vol. 19, (2002), pp. 119–124.

    Article  CAS  Google Scholar 

  13. R.G Konsler, J. Kaarl and E.N. Jacobsen: “Cooperative asymmetric catalysis with dimeric salen complexes”, J. Am. Chem. Soc., Vol. 120, (1998), pp. 10780–10781.

    Article  CAS  Google Scholar 

  14. M. Tokunaga, J.F. Larrow, F. Kakuchi and E.N. Jacobsen: “Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis”, Science, Vol. 277, (1997), pp. 936–938.

    Article  CAS  Google Scholar 

  15. K.B. Hansen, J.L. Leighton and E.N. Jacobsen: “On the mechanism of asymmetric nucleophilic ring-opening of epoxides catalyzed by (salen)Cr-III complexes”, J. Am. Chem. Soc., Vol. 118, (1996), pp. 10924–10925.

    Article  CAS  Google Scholar 

  16. D.A. Annis and E.N. Jacobsen: “Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides”, J. Am. Chem. Soc., Vol. 121, (1999), pp. 4147–4154.

    Article  CAS  Google Scholar 

  17. I. Guray, J. Warzywoda, N. Bac and A. Sacco, Jr.: “Synthesis of zeolite MCM-22 under rotating and static conditions”, Microporous Mesoporous Mater., Vol. 31, (1999), pp. 241–251.

    Article  CAS  Google Scholar 

  18. F. Notheisz, Á. Zsigmond, Zs. Szegletes and J.E. Bäckvall: “Aerobic oxidations on metal macrocycles encapsulated in zeolites”, Studies in Surface Science and Catalysis, Vol. 94, (1995), pp. 728–735.

    Article  Google Scholar 

  19. Á. Zsigmond, F. Notheisz and J.E. Bäckvall: “Rate enhancement of oxidation reactions by the encapsulation of metal phthalocyanine complex”, Catal. Lett., Vol. 65, (2000), pp. 135–139.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, 6720, Szeged, Hungary

    Krisztián Bogár

  2. Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, SE-106 91, Stockholm, Sweden

    Krisztián Bogár

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  1. Krisztián Bogár
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Bogár, K. Oxidation of α-methylstyrene on an MCM-22 encapsulated (R, R)-(−)-N, N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) catalyst. cent.eur.j.chem. 3, 63–71 (2005). https://doi.org/10.2478/BF02476238

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  • DOI: https://doi.org/10.2478/BF02476238

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