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Tetrahydropyranylation of Alcohols in the Presence of a Slightly Basic, Heterogeneous Titanium Catalyst

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Abstract

4 Å molecular sieve modified with titanium(IV) is an efficient heterogeneous catalyst for the tetrahydropyranylation of alcohols under mild, slightly basic reaction conditions. The catalyst can be reused with good yield after a simple treatment with dichloromethane.

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References

  1. Sartoni G, Ballini R, Bigi F, Bosica G, Maggi R, Righi P (2004) Chem Rev 104:199–250

    Article  Google Scholar 

  2. Forrest Woods G, Kramer DN (1947) J Am Chem Soc 69:2246

    Article  Google Scholar 

  3. Bernady KF, Floyd MB, Poletto JE, Weiss MJ (1979) J Org Chem 44:1438–1447

    Article  CAS  Google Scholar 

  4. Alper H, Dinkes L (1972) Synthesis 81–82

  5. Rezai N, Meybodi FA, Salehi P (2000) Synth Commun 30:1799–1805

    Article  CAS  Google Scholar 

  6. Chandrasekhar S, Takhi M, Reddy YR, Mohapatra S, Rao CR, Reddy KV (1997) Tetrahedron 53:14997

    Article  CAS  Google Scholar 

  7. Haynes LJ, Plimmer JR (1956) J Chem Soc 4665

  8. Molnár Á, Beregszászi T (1996) Tetrahedron Lett 37:8597–8600

    Article  Google Scholar 

  9. Kumar P, Dinesh CU, Reddy RS, Pandey B (1993) Synthesis 1069–1070

  10. Hegedüs A, Vígh I, Hell Z (2004) Synth Comm 34(22):4145–4152

    Article  Google Scholar 

  11. Hoyer S, Laszlo P, Orlovri M, Polla E (1986) Synthesis 655–657

  12. Miyashita M, Yoshikoshi A, Grieco PA (1977) J Org Chem 42:3772–3774

    Article  CAS  Google Scholar 

  13. Bandgar BP, Sadavarte VS, Uppalla LS, Patil SV (2003) Monatshefte 134:425–428

    Article  CAS  Google Scholar 

  14. Khazaei A, Rostami A, Mahboubifar M (2007) Catalysis Comm 8:383–388

    Article  CAS  Google Scholar 

  15. Kotke M, Schreiner PR (2007) Synthesis 779–790

  16. Chaturverdi D, Kumar A, Ray S (2004) Indian J Chem SecB 43:437–438

    Google Scholar 

  17. Cwik A, Hell Z, Figueras F (2006) Adv Synth Catal 348:523–530

    Article  CAS  Google Scholar 

  18. Cwik A, Hell Z, Figueras F (2006) Tetrahedron Lett 47:3023–3026

    Article  CAS  Google Scholar 

  19. Cwik A, Hell Z, Figueras F (2005) Org Biomol Chem 3:4307–4309

    Article  CAS  Google Scholar 

  20. Németh J, Hell Z (2013) React Kinet Mech Catal 111:115–121

    Article  Google Scholar 

  21. Kiss A, Hell Z, Bálint M (2010) Org Biomol Chem 8:331–335

    Article  CAS  Google Scholar 

  22. Fodor A, Kiss A, Debreczeni N, Hell Z, Gresits I (2010) Org Biomol Chem 8:4575–4581

    Article  CAS  Google Scholar 

  23. Kiss A, Hell Z (2013) Synth Comm 43:1778–1786

    Article  CAS  Google Scholar 

  24. Kiss A, Hell Z (2011) Tetrahedron Lett 52:6021–6023

    Article  CAS  Google Scholar 

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Acknowledgments

Á. M. is grateful to Chinoin Pharmaceuticals Ltd. for the financial support. The authors express their gratitude to Prof. K. László for the gas adsorption measurements. This work was financially supported by the New Széchenyi Development Plan (TÁMOP-4.2.1/B-09/1/KMR-2010-0002).

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Correspondence to Zoltán Hell.

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Magyar, Á., Nagy, B. & Hell, Z. Tetrahydropyranylation of Alcohols in the Presence of a Slightly Basic, Heterogeneous Titanium Catalyst. Catal Lett 145, 1876–1879 (2015). https://doi.org/10.1007/s10562-015-1590-8

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  • DOI: https://doi.org/10.1007/s10562-015-1590-8

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