Catalysis Letters

, Volume 138, Issue 3–4, pp 155–159 | Cite as

Microwave-Assisted Nafion-H Catalyzed Friedel–Crafts Type Reaction of Aromatic Aldehydes with Arenes: Synthesis of Triarylmethanes

  • Surya G. K. Prakash
  • Gabriella Fogassy
  • George A. Olah
Article

Abstract

A new solid acid Nafion-H, a perfluorinated sulfonic acid resin, catalyzed microwave-assisted synthesis of triarylmethanes is described. Various benzaldehydes react readily with arenes to provide the corresponding triarylmethanes in good to excellent yields. The reactions were carried out under solvent free conditions under microwave irradiation in a pressure vessel. The solvent free microwave irradiation methods appears to be an environmentally friendly synthetic protocol providing products in significantly shorter reaction times over traditional heating methods carried out in a pressure tube.

Graphical Abstract

Keywords

Nafion-H Microwave irradiation Arylation Triarylmethanes Benzaldehyde 

Notes

Acknowledgments

Financial support provided by the Loker Hydrocarbon Research Institute is gratefully acknowledged.

References

  1. 1.
    Loupy A (2002) Microwaves in organic synthesis. Wiley-VCH, WeinheimCrossRefGoogle Scholar
  2. 2.
    Kappe CO, Stadler A (2005) Microwaves in organic and medicinal chemistry. Wiley-VCH, WeinheimCrossRefGoogle Scholar
  3. 3.
    Tierney JP, Lidstrom P (2005) Microwave assisted organic synthesis. Blackwell, OxfordCrossRefGoogle Scholar
  4. 4.
    Lidström P, Tierney J, Walthey B, Westman J (2001) Tetrahedron 57:9225–9283CrossRefGoogle Scholar
  5. 5.
    Kappe CO, Dallinger D (2009) Mol Divers 13:71–193CrossRefGoogle Scholar
  6. 6.
    Li Z, Duan Z, Kang J, Wang H, Yu L, Wu Y (2008) Tetrahedron 64:1924–1930CrossRefGoogle Scholar
  7. 7.
    Griepentorg H (1886) Berg Dtsch Chem Ges 19:1876CrossRefGoogle Scholar
  8. 8.
    Schaarschmidt A, Hermann L, Szemzo B (1925) Ber Dtsch Chem Ges 58:1914CrossRefGoogle Scholar
  9. 9.
    Hoffmann JE, Schriesheim A (1964) In: Olah GA (ed) Friedel–Crafts and related reactions, vol II. Wiley-Interscience, New York, pp 597–640Google Scholar
  10. 10.
    Hey JD (1935) J Chem Soc 72Google Scholar
  11. 11.
    Hey JD, Ellison H (1938) J Chem Soc 1847Google Scholar
  12. 12.
    Ungnade HF, Crandall EW (1949) J Am Chem Soc 71:2209CrossRefGoogle Scholar
  13. 13.
    Ungnade HF, Kline EF, Crandall EW (1949) J Am Chem Soc 75:333Google Scholar
  14. 14.
    Gattermann J, Koch JA (1897) Chem Ber 30:1622CrossRefGoogle Scholar
  15. 15.
    Olah GA (1964) Friedel–Crafts and related reactions, vol III, Chapter 38. Wiley-Interscience, New YorkGoogle Scholar
  16. 16.
    Schubert WM, Latourette HK (1952) J Am Chem Soc 74:1879Google Scholar
  17. 17.
    Burkett H, Schubert WM, Schultz F, Murphy RB, Talbott R (1959) J Am Chem Soc 81:3923CrossRefGoogle Scholar
  18. 18.
    Robertson RM, El-Khawaga AM, Swenney KM, El-Zohry MF (1987) J Org Chem 52:1591CrossRefGoogle Scholar
  19. 19.
    Olah GA, Rasul G, York C, Prakash GKS (1995) J Am Chem Soc 117:11211CrossRefGoogle Scholar
  20. 20.
    Olah GA, Prakash GKS, Molnár A, Sommer J (2009) Superacid chemistry, 2nd edn. Wiley, New YorkGoogle Scholar
  21. 21.
    Prakash GKS, Paknia F, Chacko S, Mathew T, Olah GA (2008) Heterocycles 76:783CrossRefGoogle Scholar
  22. 22.
    Prakash GKS, Panja C, Shakhmin A, Shah E, Mathew T, Olah GA (2009) J Org Chem 74:8659CrossRefGoogle Scholar
  23. 23.
    Olah GA, Iyer PS, Prakash GKS (1986) Synthesis 513Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Surya G. K. Prakash
    • 1
  • Gabriella Fogassy
    • 1
  • George A. Olah
    • 1
  1. 1.Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of ChemistryUniversity of Southern CaliforniaLos AngelesUSA

Personalised recommendations