Skip to main content
SpringerLink
Log in

Oxidovanadium(IV) Complexes of 3-Hydroxy-4-pyrone and 3-Hydroxy-4-pyridinone Ligands: A New Generation of Homogeneous Catalysts for the Epoxidation of Geraniol

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A novel generation of homogeneous catalysts for the epoxidation of geraniol, in the presence of tert-butyl hydroperoxide oxidant is reported. Oxidovanadium(IV) complexes of 3-hydroxy-4-pyrone and 3-hydroxy-4-pyridinone ligands exhibit excellent activity and selectivity towards the 2,3-epoxygeraniol product, only differing in the reaction times and turnover frequencies. The pyrone based complexes are the most efficient catalysts showing performances similar to that of the well known oxidovanadium(IV) acetylacetonate catalyst.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Gates BC (1992) Catalytic chemistry. Wiley, New York

    Google Scholar 

  2. Parshall GW, Itel SD (1992) Homogeneous catalysis. Wiley, New York

    Google Scholar 

  3. van Leeuwen PW (2005) Homogeneous catalysis: understanding the art. Springer, London

    Google Scholar 

  4. Xia Q-H, Ge H-Q, Ye C-P, Liu Z-M, Su K-X (2005) Chem Rev 105:1603–1662

    Article  CAS  Google Scholar 

  5. Gupta KC, Sutar AK (2008) Coord Chem Rev 252:1420–1450

    Article  CAS  Google Scholar 

  6. Adão P, Pessoa JC, Henriques RT, Kuznetsov ML, Avecilla F, Maurya MR, Kumar U, Correia I (2009) Inorg Chem 48:3542–3561

    Article  Google Scholar 

  7. Kuznetsov ML, Pessoa JC (2009) Dalton Trans 5460–5468

  8. Adão P, Maurya MR, Kumar U, Avecilla F, Henriques RT, Kusnetsov ML, Pessoa JC, Correia I (2009) Pure Appl Chem 81:1279–1296

    Article  Google Scholar 

  9. Matsumoto K, Saito B, Katsuki T (2007) Chem Commun 3619–3627

  10. Ligtenbarg AGJ, Hage R, Feringa BL (2003) Coord Chem Rev 237:89–101

    Article  CAS  Google Scholar 

  11. Bolm C (2003) Coord Chem Rev 237:245–256

    Article  CAS  Google Scholar 

  12. Conte V, di Furia F, Licini G (1997) Appl Catal A General 157:335–361

    Article  CAS  Google Scholar 

  13. Butler A, Clague MJ, Meister GE (1994) Chem Rev 94:625–638

    Article  CAS  Google Scholar 

  14. Sharpless KB, Michaelson RC (1973) J Am Chem Soc 95:6136–6137

    Article  CAS  Google Scholar 

  15. Rossiter BE, Verhoeven TR, Sharpless KB (1979) Tetrahedron Lett 20:4733–4736

    Article  Google Scholar 

  16. Itoh T, Jitsukawa K, Kaneda K, Teranishi S (1979) J Am Chem Soc 101:159–169

    Article  CAS  Google Scholar 

  17. Sharpless KB, Verhoeven TR (1979) Aldrichimica Acta 12:63–74

    CAS  Google Scholar 

  18. Michaelson RC, Palermo RE, Sharpless KB (1977) J Am Chem Soc 99:1990–1992

    Article  CAS  Google Scholar 

  19. Murase N, Hoshino Y, Oishi M, Yamamoto H (1999) J Org Chem 64:338–339

    Article  CAS  Google Scholar 

  20. Makita N, Hoshino Y, Yamamoto H (2003) Angew Chem Int Ed 42:941–943

    Article  CAS  Google Scholar 

  21. Hoshino Y, Yamamoto H (2000) J Am Chem Soc 122:10452–10453

    Article  CAS  Google Scholar 

  22. Bryliakov KP, Talsi EP, Kühn T, Bolm C (2003) New J Chem 27:609–614

    Article  CAS  Google Scholar 

  23. Wu H-L, Uang B-J (2002) Tetrahedron Asymmetr 13:2625–2628

    Article  CAS  Google Scholar 

  24. Malkov AV, Czemerys L, Malyshev DA (2009) J Org Chem 74:3350–3355

    Article  CAS  Google Scholar 

  25. Bourhani Z, Malkov AV (2005) Chem Commun 4592–4594

  26. Malkov AV, Bourhani Z, Kočovsky P (2005) Org Biomol Chem 3:3194–3200

    Article  CAS  Google Scholar 

  27. Li Z, Zhang W, Yamamoto H (2008) Angew Chem Int Ed 47:7520–7522

    Article  CAS  Google Scholar 

  28. Zhang W, Yamamoto H (2007) J Am Chem Soc 129:286–287

    Article  CAS  Google Scholar 

  29. Barlan AU, Zhang W, Yamamoto H (2007) Tetrahedron 63:6075–6087

    Article  CAS  Google Scholar 

  30. Zhang W, Basak A, Kosugi Y, Hoshino Y, Yamamoto H (2005) Angew Chem Int Ed 44:4389–4391

    Article  CAS  Google Scholar 

  31. Lattanzi A, Piccirillo S, Scettri A (2005) Eur J Org Chem 1669–1674

  32. Adam W, Beck AK, Pichota A, Saha-Möller CR, Seebach D, Vogl N, Zhang R (2003) Tetrahedron Asymmetr 14:1355–1361

    Article  CAS  Google Scholar 

  33. Thompson KH, Orvig C (2004) Met Ions Biol Syst 41:221–252

    CAS  Google Scholar 

  34. Thompson KH, Orvig C (2006) J Inorg Biochem 100:1925–1935

    Article  CAS  Google Scholar 

  35. Thompson KH, Lichter JB, LeBel C, Caife MS, McNeil JH, Orvig C (2009) J Inorg Biochem 103:554–558

    Article  CAS  Google Scholar 

  36. Rangel M, Tamura A, Fukushima C, Sakurai H (2001) J Biol Inorg Chem 6:128–132

    Article  CAS  Google Scholar 

  37. Rehder D, Costa Pessoa J, Geraldes CFGC, Castro MMCA, Kabanos T, Kiss T, Meier B, Micera G, Pettersson L, Rangel M, Salifoglou A, Turel I, Wang D (2002) J Biol Inorg Chem 7:384–396

    Article  CAS  Google Scholar 

  38. Rangel M, Leite A, Amorim MJ, Garriba E, Micera G, Lodyga-Chruscinska E (2006) Inorg Chem 45:8086–8097

    Article  CAS  Google Scholar 

  39. Rangel M, Amorim MJ, Nunes A, Leite A, Pereira E, de Castro B, Sousa C, Yoshikawa Y, Sakurai H (2009) J Inorg Biochem 103:496–502

    Article  CAS  Google Scholar 

  40. Burgess J, Rangel M (2008) Adv Inorg Chem 60:167–243

    Article  CAS  Google Scholar 

  41. Martins RRL, Neves MGPMS, Silvestre AJD, Simões MMQ, Silva AMS, Tomé AC, Cavaleiro JAS, Tagliatesta P, Cresini C, Mol J (2001) Catal A Chem 172:33–42

    Article  CAS  Google Scholar 

  42. Pereira C, Biernacki K, Rebelo SLH, Magalhães AL, Carvalho AP, Pires J, Freire C, Mol J (2009) Catal A Chem 312:53–64

    Article  CAS  Google Scholar 

  43. Pereira C, Silva AR, Carvalho AP, Pires J, Freire C, Mol J (2008) Catal A Chem 283:5–14

    Article  CAS  Google Scholar 

  44. Jarrais B, Pereira C, Silva AR, Carvalho AP, Pires J, Freire C (2009) Polyhedron 28:994–1000

    Article  CAS  Google Scholar 

  45. Jarrais B, Silva AR, Freire C (2005) Eur J Inorg Chem 4582–4589

Download references

Acknowledgments

This work was funded by Fundação para a Ciência e a Tecnologia (FCT) and FEDER, through project ref. PTDC/CTM/65718/2006. C.P. and A.L. thank FCT for a PhD fellowship. The NMR spectrometer used in this work is part of the National NMR Network and was purchased in the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005, with funds from POCI 2010 (FEDER) and FCT.

Author information

Authors and Affiliations

  1. REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 4169-007, Porto, Portugal

    Clara Pereira, Andreia Leite, Ana Nunes, Susana L. H. Rebelo & Cristina Freire

  2. REQUIMTE, Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, 4099-003, Porto, Portugal

    Maria Rangel

Authors
  1. Clara Pereira
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Andreia Leite
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ana Nunes
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Susana L. H. Rebelo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Maria Rangel
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Cristina Freire
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Cristina Freire.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 233 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pereira, C., Leite, A., Nunes, A. et al. Oxidovanadium(IV) Complexes of 3-Hydroxy-4-pyrone and 3-Hydroxy-4-pyridinone Ligands: A New Generation of Homogeneous Catalysts for the Epoxidation of Geraniol. Catal Lett 135, 98–104 (2010). https://doi.org/10.1007/s10562-010-0281-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-010-0281-8

Keywords

Search

Navigation