Abstract
Phosphonium ionic liquid (IL)—trihexyl-tetradecylphosphonium bis(trifluoromethylsulfonyl)imide, has been tested as the medium in the Diels–Alder reaction between cyclopentadiene and dienophiles from the group of α,β-unsaturated esters, aldehydes and ketones. Catalytic activities of a few metal chlorides, triflates and bis-triflimides in this reaction have been compared. The recycling of the catalyst with phosphonium IL was studied.
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Berlin PA, Watson KJ, Nguyen ST (2004) Macromolecules 37:8364–8372
(a)Owen RM, Gestwicki JE, Young T, Kiessling LL (2002) Org Lett 4:142293–142296; (b) Gestwicki JE, Strong LE, Cairo CW, Boehm FJ, Kiessling LL (2002) Chem Biol 2:163–169; (c)Maynard HD, Okada SY, Grubbs RH (2001) J Am Chem Soc 123:1275–1279
(a) Buchmeiser MR (2000) Chem Rev 100:1565–1604 and references therein; (b) Meyers A, South C, Weck M (2004) Chem Commun 1176; (c) Meyers A, Weck M (2004) Chem Mater 16:1183; (d) Meyers A, Weck M (2003) Macromolecules 36:1766
(a) Arehart SV, Pugh C (1997) J Am Chem Soc 119:3027; (b) Weck M, Mohr B, Maughon BR, Grubbs RH (1997) Macromolecules 30:6430; (c) Wewerka K, Wewerka A, Stelzer F, Gallot B, Andruzzi L, Galli G (2003) Macromol Rapid Commun 24:906
Raimundo J-M, Lecomte S, Edelman MJ, Consilio S, Biaggio I, Bosshard C, Guenter P, Diederich F (2004) J Mater Chem 14:292
(a) Rideout DC, Breslow R (1980) J Am Chem Soc 102:7816; (b) Grieco PA, Yoshida K, Garner P (1983) J Org Chem 48:3137; (c) Breslow R, Maitra U (1984) Tetrahedron Lett 25:1239; (d) Pindur U, Luft G, Otto C (1993) Chem Rev 93:741–761; (e) Kumar A (2001) Chem Rev 101:1
(a) Holbrey JD, Seddon KR (1999) Clean Prod Process 1:223–236; (b) Clark JH, Tavener SJ (2007) Org Process Res Dev 11:149–155
(a) Welton T (1999) Chem Rev 99:2071–2083; (b) Welton T (2004) Coordin Chem Rev 248:2459–2477
(a) Lopez I, Silvero G, Arevalo MJ, Babiano R, Palacios JC, Bravo JL (2007) Tetrahedron 63:2901–2906; (b) Silvero G, Arevalo MJ, Bravo JL, Avalos M, Jimenez JL, Lopez I (2005) Tetrahedron 61:7105–7111; (c) Fu F, Teo Y-Ch, Loh T-P (2006) Org Lett 8:5999–6001; (d) Yadav JS, Reddy BVS, Kondaji G, Sowjanya S, Nagaiah K (2006) J Mol Catal A: Chem 258:361–366; (e) Dramska A, Antoszczyszyn M, Janus E (2006) Przem Chem 85/1:47–49; (f) Earle MJ, McCormac PB, Seddon KR (1999) Green Chem 1:23–25
Lee CW (1999) Tetrahedron Lett 40:2461–2464
Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2002) Green Chem 4:24–26
Aggarwal A, Lancaster NL, Sethi AR, Welton T (2002) Green Chem 4:517–520
Janus E, Goc-Maciejewska I, Łożyński M, Pernak J (2006) Tetrahedron Lett 47:4079–4083
(a) McNulty J, Cheekoori S, Nair JJ, Larichev V, Capretta A, Robertson Al J (2005) Tetrahedron Lett 46:3641–3644; (b) Cieniecka-Rosłonkiewicz A, Pernak J, Kubis-Feder J, Ramani A, Robertson AJ, Seddon K (2005) Green Chem 7:855–862; (c) McNulty J, Nair JJ, Cheekoori S, Larichev V, Capretta A, Robertson Al J (2006) Chem Eur J 12:9314–9322; (d) Bonnet LG, Kariuki BM (2006) Eur J Inorg Chem 437–446; (e) McNulty J, Cheekoori S, Bender TP, Coggan JA (2007) Eur J Org Chem 1423–1428; (f) Fergusson L, Scovazzo P (2007) Ind Eng Chem Res 46:1369–1374
(a) Bradaric CJ, Downard A, Kennedy C, Robertson AJ, Zhou Y (2003) Green Chem 5:143–152; (b) Tsunashima K, Sugiya M (2007) Electrochem Commun 9:2353–2358; (c) Chowdhury S, Mohan RS, Scott JL (2007) Tetrahedron 63:2363–2389
(a) Hagiwara R, Ito Y (2000) Fluorine Chem 105:221; (b) Matsumoto H, Yanagida M, Tanimoto K, Nomura M, Kitagawa Y, Miyazaki Y (2000) Chem Lett 29:922
Swatloski RP, Holbrey JD, Rogers RD (2003) Green Chem 5:361–363
Ferguson L, Scovazzo P (2007) Ind Eng Chem Res 46:1369–1374
(a) Ludley P, Karodia N (2001) Tetrahedron Lett 42:2011–2014; (b) Ludley P, Karodia N (2002) ARKIVOC (iii) 172–175
(a) Kobayashi S, Morikawa M, Ishitani H (1995) Synlett 1153–1154; (b) Kobayashi S, Sugiura M, Kitagawa H, Lam WW-L (2002) Chem Rev 102:2227–2302; (c) Kobayashi H, Nie J, Sonoda T (1995) Chem Lett 24:307
Binnemans K (2007) Chem Rev 107:2592–2614 and references therein
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The research was supported by Polish grant No. N205 055 31/2491.
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Janus, E., Stefaniak, W. The Diels–Alder Reaction in Phosphonium Ionic Liquid Catalysed by Metal Chlorides, Triflates and Triflimides. Catal Lett 124, 105–110 (2008). https://doi.org/10.1007/s10562-008-9431-7
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DOI: https://doi.org/10.1007/s10562-008-9431-7