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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Starks CM, Liotta CL, Halpern M (1994) Phase-transfer catalysis: fundamentals applications and industrial perspectives. Chapman & Hall, New York
Weber WP, Gokel GW (1977) Phase transfer catalysis in organic synthesis. Springer, New York
Kiasat AR, Nazari S (2013) J Incl Phenom Macrocycl Chem 76:363
Yang HM, Wu PI, Li CM (2000) Appl Catal A 193:129
Chakrabarty M, Karmakar S, Mukherjee R, Arima S, Harigaya Y (2009) Monatsh Chem 140:375
Shimizu S, Shimada N, Sasaki Y (2006) Green Chem 8:608
Shirakawa S, Shimizu S (2008) Synlett 10:1539
Akceylan E, Yilmaz M (2011) Tetrahedron 67:6240
Moll HE, Semeril D, Matt D, Toupet L, Harrowfield JJ (2012) Org Biomol Chem 10:372
Mustafina AR, Zakharova LY, Elistratova JG, Voronin MA, Syakaev VV, Konovalov AI (2009) J Colloid Interface Sci 333:613
Konovalov AI, Antipin IS (2008) Mendeleev Commun 18:229
Zakharova LY, Mustafina AR, Valeeva FG, Ibragimova AR, Ablakova YR, Elistratova YG, Syakaev VV, Kudryavtseva LA, Konovalov AI (2008) Colloid J 70:444
Davis F, Faul CFJ, Higson SPJ (2009) Soft Matter 5:2746
Mouradzadegun A, Kiasat AR, Kazemian Fard P (2012) Catal Commun 29:1
Mouradzadegun A, Gheitasvand N (2005) Phosphorus. Sulfur Silicon Relat Elem 180:1385
Ganjali MR, Norouzi P, Emami M, Golmohamadi M, Pirelahi H, Mouradzadegun A (2006) J Chin Chem Soc 53:1209
Mouradzadegun A, Dianat Sh (2009) J Heterocycl Chem 46:778
Mouradzadegun A, Ghasem Hezave F, Karimnia M (2010) Phosphorus Sulfur Silicon Relat Elem 185:84
Kiasat AR, Mouradzadegun A, Elahi S, Fallah-Mehrjardi M (2010) Chin Chem Lett 21:146
Mouradzadegun A, Abadast F (2013) Tetrahedron Lett 54:2641
Mouradzadegun A, Abadast F (2013) Monatsh Chem 144:375
Mouradzadegun A, Abadast F (2014) Synth Commun 44:640
Mouradzadegun A, Abadast F (2014) Synlett 25:448
Balaban AT, Tudose A, Caproiu MT (2003) Tetrahedron 59:3291
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
Karade NN, Gampawar SV, Kondre JM, Shinde SV (2008) Tetrahedron Lett 49:402
Sabitha G, Prasad MN, Ramesh M, Yadav JS (2010) Monatsh Chem 141:1245
Clark B, Capon RJ, Lacey E, Tennant S, Gill JH, Bulheller B, Bringmann G (2005) J Nat Prod 68:1226
Wu J, Zhu Q, Wang L, Fathi R, Yang Z (2003) J Org Chem 68:670
Abis L, Dalcanale E, Vosel AD, Spera S (1988) J Org Chem 53:5475
Hoegberg AGS (1980) J Am Chem Soc 102:6046
Schneider H-J, Guttes D, Schneider U (1986) Angew Chem Int Ed 25:647
Schneider H-J, Schneider U (1987) J Org Chem 52:1613
Inouye M, Hashimoto K, Isagawa K (1994) J Am Chem Soc 116:5517
Schneider H-J, Guttes D, Schneider U (1988) J Am Chem Soc 110:6449
Mustafina AR, Elistratova YG, Syakaev VV, Amirov RR, Konovalov AI (2006) Russ Chem Bull Int Ed 55:1419
Amat AM, Arques A, Bossmann SH, Braun AM, Gob S, Miranda MA (2003) Angew Chem Int Ed 42:1653
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
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
Tunstad LM, Tucker JA, Dalcanale E, Weiser J, Bryant JA, Sherman JC, Helgeson RC, Knobler CB, Cram DJ (1989) J Org Chem 54:1305
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This work was supported by the Research Council at the University of Shahid Chamran.
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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