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Tetraphenolate c-methylcalix[4]resorcinarene as a new heterogeneous phase transfer catalyst for ring-opening of triaryl substituted pyrylium salts in aqueous biphasic medium

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Abstract

This study reports, for the first time, the application of water-insoluble tetraphenolate c-methylcalix[4]resorcinarene as an efficient and heterogeneous phase transfer catalyst at room temperature. This supramolecule could facilitate the nucleophilic reactions through the formation of a host–guest complex in the organic-aqueous interfacial layer. Moreover, the recovered catalyst can be used for several times without serious decrease in activity.

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References

  1. Starks CM, Liotta CL, Halpern M (1994) Phase-transfer catalysis: fundamentals applications and industrial perspectives. Chapman & Hall, New York

    Book  Google Scholar 

  2. Weber WP, Gokel GW (1977) Phase transfer catalysis in organic synthesis. Springer, New York

    Book  Google Scholar 

  3. Kiasat AR, Nazari S (2013) J Incl Phenom Macrocycl Chem 76:363

    Article  CAS  Google Scholar 

  4. Yang HM, Wu PI, Li CM (2000) Appl Catal A 193:129

    Article  CAS  Google Scholar 

  5. Chakrabarty M, Karmakar S, Mukherjee R, Arima S, Harigaya Y (2009) Monatsh Chem 140:375

    Article  CAS  Google Scholar 

  6. Shimizu S, Shimada N, Sasaki Y (2006) Green Chem 8:608

    Article  CAS  Google Scholar 

  7. Shirakawa S, Shimizu S (2008) Synlett 10:1539

    Google Scholar 

  8. Akceylan E, Yilmaz M (2011) Tetrahedron 67:6240

    Article  CAS  Google Scholar 

  9. Moll HE, Semeril D, Matt D, Toupet L, Harrowfield JJ (2012) Org Biomol Chem 10:372

    Article  Google Scholar 

  10. Mustafina AR, Zakharova LY, Elistratova JG, Voronin MA, Syakaev VV, Konovalov AI (2009) J Colloid Interface Sci 333:613

    Article  CAS  Google Scholar 

  11. Konovalov AI, Antipin IS (2008) Mendeleev Commun 18:229

    Article  CAS  Google Scholar 

  12. Zakharova LY, Mustafina AR, Valeeva FG, Ibragimova AR, Ablakova YR, Elistratova YG, Syakaev VV, Kudryavtseva LA, Konovalov AI (2008) Colloid J 70:444

    Article  CAS  Google Scholar 

  13. Davis F, Faul CFJ, Higson SPJ (2009) Soft Matter 5:2746

    Article  CAS  Google Scholar 

  14. Mouradzadegun A, Kiasat AR, Kazemian Fard P (2012) Catal Commun 29:1

    Article  CAS  Google Scholar 

  15. Mouradzadegun A, Gheitasvand N (2005) Phosphorus. Sulfur Silicon Relat Elem 180:1385

    Article  CAS  Google Scholar 

  16. Ganjali MR, Norouzi P, Emami M, Golmohamadi M, Pirelahi H, Mouradzadegun A (2006) J Chin Chem Soc 53:1209

    CAS  Google Scholar 

  17. Mouradzadegun A, Dianat Sh (2009) J Heterocycl Chem 46:778

    Article  CAS  Google Scholar 

  18. Mouradzadegun A, Ghasem Hezave F, Karimnia M (2010) Phosphorus Sulfur Silicon Relat Elem 185:84

    Article  CAS  Google Scholar 

  19. Kiasat AR, Mouradzadegun A, Elahi S, Fallah-Mehrjardi M (2010) Chin Chem Lett 21:146

    Article  CAS  Google Scholar 

  20. Mouradzadegun A, Abadast F (2013) Tetrahedron Lett 54:2641

    Article  CAS  Google Scholar 

  21. Mouradzadegun A, Abadast F (2013) Monatsh Chem 144:375

    Article  CAS  Google Scholar 

  22. Mouradzadegun A, Abadast F (2014) Synth Commun 44:640

    Article  CAS  Google Scholar 

  23. Mouradzadegun A, Abadast F (2014) Synlett 25:448

    Article  Google Scholar 

  24. Balaban AT, Tudose A, Caproiu MT (2003) Tetrahedron 59:3291

    Article  CAS  Google Scholar 

  25. Harris LJ, Alexander NJ, Saparno A, Blackwell B, McCormick SP, Desjardins AE, Robert LS, Tinker N, Hattori J, Piché C, Schernthaner JP, Watson R, Ouellet T (2007) Fungal Genet Biol 44:293

    Article  CAS  Google Scholar 

  26. Karade NN, Gampawar SV, Kondre JM, Shinde SV (2008) Tetrahedron Lett 49:402

    Google Scholar 

  27. Sabitha G, Prasad MN, Ramesh M, Yadav JS (2010) Monatsh Chem 141:1245

    Article  CAS  Google Scholar 

  28. Clark B, Capon RJ, Lacey E, Tennant S, Gill JH, Bulheller B, Bringmann G (2005) J Nat Prod 68:1226

    Article  CAS  Google Scholar 

  29. Wu J, Zhu Q, Wang L, Fathi R, Yang Z (2003) J Org Chem 68:670

    Article  CAS  Google Scholar 

  30. Abis L, Dalcanale E, Vosel AD, Spera S (1988) J Org Chem 53:5475

    Article  CAS  Google Scholar 

  31. Hoegberg AGS (1980) J Am Chem Soc 102:6046

    Article  CAS  Google Scholar 

  32. Schneider H-J, Guttes D, Schneider U (1986) Angew Chem Int Ed 25:647

    Article  Google Scholar 

  33. Schneider H-J, Schneider U (1987) J Org Chem 52:1613

    Article  CAS  Google Scholar 

  34. Inouye M, Hashimoto K, Isagawa K (1994) J Am Chem Soc 116:5517

    Article  CAS  Google Scholar 

  35. Schneider H-J, Guttes D, Schneider U (1988) J Am Chem Soc 110:6449

    Article  CAS  Google Scholar 

  36. Mustafina AR, Elistratova YG, Syakaev VV, Amirov RR, Konovalov AI (2006) Russ Chem Bull Int Ed 55:1419

    Article  CAS  Google Scholar 

  37. Amat AM, Arques A, Bossmann SH, Braun AM, Gob S, Miranda MA (2003) Angew Chem Int Ed 42:1653

    Article  CAS  Google Scholar 

  38. Balaban AT, Dinculescu A, Dorofeenko GN, Fischer GW, Koblik AV, Mezheritskii VV, Schroth W (1982) In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 2, suppl 1. Academic Press, New York

    Google Scholar 

  39. Balaban AT, Schroth W, Fischer GW (1969) In: Katritzky AR (ed) Pyrylium salts. Advances in heterocyclic chemistry, vol 10. Academic Press, New York, p 241

  40. Tunstad LM, Tucker JA, Dalcanale E, Weiser J, Bryant JA, Sherman JC, Helgeson RC, Knobler CB, Cram DJ (1989) J Org Chem 54:1305

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the Research Council at the University of Shahid Chamran.

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Correspondence to Arash Mouradzadegun.

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Mouradzadegun, A., Abadast, F. & Elahi, S. Tetraphenolate c-methylcalix[4]resorcinarene as a new heterogeneous phase transfer catalyst for ring-opening of triaryl substituted pyrylium salts in aqueous biphasic medium. Monatsh Chem 145, 1663–1667 (2014). https://doi.org/10.1007/s00706-014-1235-4

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  • DOI: https://doi.org/10.1007/s00706-014-1235-4

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