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Copper nitrate/acetic acid as an efficient synergistic catalytic system for the chemoselective tetrahydropyranylation of alcohols and phenols

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Abstract

Tetrahydropyranylation of alcohols and phenols was accomplished successfully using copper nitrate and acetic acid as a synergistic catalyst at room temperature under solvent-free condition. Compared with other synergistic catalytic systems, copper nitrate/acetic acid proved to be the most efficient. Both alcohols (primary, secondary, tertiary, benzylic, cyclic, allyl, cinnamyl, and furyl) and phenols reacted smoothly in high yields.

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References

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

    Article  CAS  Google Scholar 

  2. Greene TW, Wuts PGM (1991) Protective groups in organic synthesis, 2nd edn. Wiley, New York

    Google Scholar 

  3. Wang B, Yang LM, Suo JS (2003) Synth Commun 33:3929

    Article  CAS  Google Scholar 

  4. Boom JH, Herschied JDM (1973) Synthesis 169

  5. Palaniappan S, Ram MS, Amarnath CA (2002) Green Chem 4:369

    Article  CAS  Google Scholar 

  6. Wang YG, Wu XX, Jiang ZY (2004) Tetrahedron Lett 45:2973

    Article  CAS  Google Scholar 

  7. Karimi B, Maleki J (2002) Tetrahedron Lett 43:5353

    Article  CAS  Google Scholar 

  8. Heravi MM, Behbahani FK, Oskooie HA, Shoar RH (2005) Tetrahedron Lett 46:2543

    Article  CAS  Google Scholar 

  9. Naik S, Gopinath R, Patel BK (2001) Tetrahedron Lett 42:7679

    Article  CAS  Google Scholar 

  10. Choudary BM, Neeraja V, Kantam ML (2001) J Mol Catal A Chem 175:169

    Article  CAS  Google Scholar 

  11. Pachamuthu K, Vankar YD (2001) J Org Chem 66:7511

    Article  CAS  Google Scholar 

  12. Shirini F, Zolfigol MA, Abri AR (2007) Chin Chem Lett 18:803

    Article  CAS  Google Scholar 

  13. Habibi MH, Tangestaninejad S, Mohammadpoor-Baltork I, Mirkhani V, Yadollahi B (2001) Tetrahedron Lett 42:2851

    Article  CAS  Google Scholar 

  14. Khan AT, Ghosh S, Choudhury LH (2005) Eur J Org Chem 4891

  15. Choi JE, Ko KY (2001) Bull Korean Chem Soc 22:1177

    CAS  Google Scholar 

  16. Shirini F, Zolfigol MA, Abedini M (2005) Bull Chem Soc Jpn 78:1982

    Article  CAS  Google Scholar 

  17. Wang M, Song ZG, Jiang H, Gong H (2008) Monatsh Chem 139:601

    Article  CAS  Google Scholar 

  18. Wang M, Song ZG, Jiang H, Gong H (2007) Monatsh Chem 138:599

    Article  CAS  Google Scholar 

  19. Woods GF, Kramer DN (1947) J Am Chem Soc 69:2246

    Article  CAS  Google Scholar 

  20. Hoyer S, Laszlo P (1986) Synthesis 655 (and references cited therein)

  21. Pierson GO, Runquist OA (1968) J Org Chem 33:2572

    Article  CAS  Google Scholar 

  22. Stephens JR, Butler PL, Clow CH, Oswald MC, Smith RC, Mohan RS (2003) Eur J Org Chem 3827

  23. Olah GA, Husain A, Singh BP (1983) Synthesis 892

  24. Khan AT, Choudhury LH, Ghosh S (2004) Tetrahedron Lett 45:7891

    Article  CAS  Google Scholar 

  25. Fife TH, Jao LK (1968) J Am Chem Soc 90:4081

    Article  CAS  Google Scholar 

  26. Parham WE, Anderson EL (1948) J Am Chem Soc 70:4187

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Bohai University, Jinzhou, China

    Min Wang

  2. Center for Science and Technology Experiment, Bohai University, Jinzhou, China

    Zhi-Guo Song

  3. Liaoning Shihua University, Fushun, China

    Hong Gong & Heng Jiang

Authors
  1. Min Wang
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  2. Zhi-Guo Song
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  3. Hong Gong
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  4. Heng Jiang
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Correspondence to Min Wang.

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Wang, M., Song, ZG., Gong, H. et al. Copper nitrate/acetic acid as an efficient synergistic catalytic system for the chemoselective tetrahydropyranylation of alcohols and phenols. Monatsh Chem 140, 177–179 (2009). https://doi.org/10.1007/s00706-008-0051-0

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  • DOI: https://doi.org/10.1007/s00706-008-0051-0

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