Skip to main content
Log in

Copper p-toluenesulfonate/acetic acid: a recyclable synergistic catalytic system for the tetrahydropyranylation of alcohols and phenols

  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Copper p-toluenesulfonate/acetic acid was found to be an efficient, chemoselective synergistic catalytic system, with catalyst loading as low as 0.3 mol% leading to clean, high-yielding tetrahydropyranylation of a variety of alcohols and phenols. By simple phase-separation, copper p-toluenesulfonate can be easily recovered and reused for several times without deterioration in catalytic activity.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  • TW Greene PGM Wuts (1991) Protective Groups in Organic Synthesis EditionNumber2 Wiley New York

    Google Scholar 

  • B Karimi J Maleki (2002) Tetrahedron Lett 43 5353 Occurrence Handle10.1016/S0040-4039(02)00892-4 Occurrence Handle1:CAS:528:DC%2BD38XltVagtr0%3D

    Article  CAS  Google Scholar 

  • Goud PM, Goud PS, Reddy KR, Ashok D (2003) J Chem Res (S):806

  • F Kazemi AR Kiasat S Ebrahimi (2002) Synth Commun 32 2483 Occurrence Handle10.1081/SCC-120003397 Occurrence Handle1:CAS:528:DC%2BD38XmtF2rtbo%3D

    Article  CAS  Google Scholar 

  • BM Choudary V Neeraja KM Lakshmi (2001) J Mol Catal A: Chem 175 169 Occurrence Handle10.1016/S1381-1169(01)00202-3 Occurrence Handle1:CAS:528:DC%2BD3MXnt1Witbo%3D

    Article  CAS  Google Scholar 

  • BP Bandgar VS Sadavarte LS Uppalla SV Patil (2003) Monatsh Chem 134 425 Occurrence Handle1:CAS:528:DC%2BD3sXht1KhsLc%3D

    CAS  Google Scholar 

  • B Tamami KP Borujeny (2004) Tetrahedron Lett 45 715 Occurrence Handle10.1016/j.tetlet.2003.11.056 Occurrence Handle1:CAS:528:DC%2BD3sXhtVSiurnJ

    Article  CAS  Google Scholar 

  • I Ledneczki M Darányi F Fülöp Á Molnár (2005) Catal Today 100 437 Occurrence Handle10.1016/j.cattod.2004.09.076 Occurrence Handle1:CAS:528:DC%2BD2MXjs1SntLs%3D

    Article  CAS  Google Scholar 

  • YG Wang XX Wu ZY Jiang (2004) Tetrahedron Lett 45 2973 Occurrence Handle10.1016/j.tetlet.2004.02.057 Occurrence Handle1:CAS:528:DC%2BD2cXitFCjsrc%3D

    Article  CAS  Google Scholar 

  • Khan AT, Ghosh S, Choudhury LH (2005) Eur J Org Chem:4891

  • T Mineno (2002) Tetrahedron Lett 43 7975 Occurrence Handle10.1016/S0040-4039(02)01864-6 Occurrence Handle1:CAS:528:DC%2BD38Xns12jurY%3D

    Article  CAS  Google Scholar 

  • M Wang H Gong H Jiang ZC Wang (2006) Synth Commun 36 1953 Occurrence Handle10.1080/00397910600633979 Occurrence Handle1:CAS:528:DC%2BD28XntFWitrk%3D

    Article  CAS  Google Scholar 

  • M Wang ZG Song H Jiang H Gong (2007) Monatsh Chem 138 599 Occurrence Handle10.1007/s00706-007-0631-4 Occurrence Handle1:CAS:528:DC%2BD2sXlslCrtrw%3D

    Article  CAS  Google Scholar 

  • MV Deaton MA Ciufolini (1993) Tetrahedron Lett 34 2409 Occurrence Handle10.1016/S0040-4039(00)60428-8 Occurrence Handle1:CAS:528:DyaK3sXksVyksb0%3D

    Article  CAS  Google Scholar 

  • HC Aspinall JS Bissett N Greeves D Levin (2002) Tetrahedron Lett 43 319 Occurrence Handle10.1016/S0040-4039(01)02115-3 Occurrence Handle1:CAS:528:DC%2BD3MXpt1Gmtr8%3D

    Article  CAS  Google Scholar 

  • O Mouhtady H Gaspard-Houghmane N Roques C Roux (2003) Tetrahedron Lett 44 6379 Occurrence Handle10.1016/S0040-4039(03)01599-5 Occurrence Handle1:CAS:528:DC%2BD3sXlvFOmtL8%3D

    Article  CAS  Google Scholar 

  • Hoyer S, Laszlo P (1986) Synthesis:655 (and references cited therein)

  • Olah GA, Husain A, Singh BP (1985) Synthesis:703 (and references cited therein)

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Min Wang.

Additional information

Correspondence: Min Wang, College of Chemistry and Chemical Engineering, Bohai University, Jinzhou, China.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, M., Song, ZG., Jiang, H. et al. Copper p-toluenesulfonate/acetic acid: a recyclable synergistic catalytic system for the tetrahydropyranylation of alcohols and phenols. Monatsh Chem 139, 601–604 (2008). https://doi.org/10.1007/s00706-007-0821-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-007-0821-0

Keywords

Navigation