An Improved Protocol for the Preparation of New 1, 2, 3 Triazolium Based Ionic Liquids and their Application as solvent for Aldol reaction

• Authors: Vivek Srivastava
• Languages of publication: EN

Abstracts

EN

Microwave heating was used to synthesise different types of 1, 2, 3
triazolium based ionic liquids (5a-j) with good yield in reduced time. These
ionic liquids were further screened as reaction medium for Aldol reaction
using two different most promising organocatalysts; proline and proline
tetrazole. In both cases, Aldol products were obtained in good yield and
selectivity with each ionic liquid. It is important to notify that all the ionic
liquids (5a-j) offer 5 times recyclability with our catalytic system (Proline or
Proline tetrazole).

Keywords

EN

Organocatalysis; Microwave; Ionic Liquid; Proline; Proline Tetrazole; Aldol reaction

• Publisher: De Gruyter Open
• Journal: Asymmetric Catalysis
• Year: 2013
• Volume: 1
• Issue: 1

Dates

online

14 - 11 - 2012

received

18 - 7 - 2012

accepted

6 - 8 - 2012

Contributors

author

Vivek Srivastava

• Area of Pure Sciences, University Campus: NIIT University, Neemrana, NH-8 Delhi-Jaipur Highway, District: Alwar, Rajasthan – 301 705

References

• S. Milmo, Chem. Ind. 2005, 4.
• T. Collins, Science 2001, 291, 48.
• E. Schuetz, Chem. Eng. Technol. 2007, 30, 685.
• Ryu, H. Matsubara, C. Emnet, J. A. Gladysz, S. Takeuchi,Y. Nakamura, D. P. Curran, Green React. Media Org. Synth.2005, 59.
• R. Breslow, Org. React. Water 2007, 1.
• J. S. Wilkes, J. Mol. Catal. A: Chem. 2004, 214, 11.
• C. Hardacre, D. Holbrey John, M. Nieuwenhuyzen, G. A.Youngs Tristan, Acc Chem Res 2007, 40, 1146.
• C. Hardacre, Editor, Special Issue: Catalysis in Ionic Liquids.In: J. Mol. Catal. A: Chem., 2008; 279(2), 2008.
• M. Haumann, A. Riisager, Chem. Rev. 2008, 108, 1474.
• Anthony, J. L.; Brennecke, J. F.; Hollberg, J. D.; Maginn, E. J.et al. in Ionic Liquids in Synthesis, Wasserscheid, P.; Welton,T. (Eds.); Wiley VCH: Weinheim, 1st ed., 2003; Vol. 1, p. 41.
• Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391.
• Vallette, H.; Ferron, L.; Coquerel, G.; Guillen, F.; Plaquevent, J.C. Arkivoc 2006, (iv), 200.
• Chiappe, C. in Ionic Liquids in Synthesis, Wasserscheid, P.;Welton, T. (Eds.); Wiley-VCH: Weinheim, 2nd ed., 2008; Vol.1, p. 265.
• Wasserscheid, P. Schulz, P. in Ionic Liquids in Synthesis,Wasserscheid, P.; Welton, T. (Eds.); Wiley-VCH: Weinheim,2nd ed., 2008; Vol. 2, p. 369.
• Ludley, P.; Karodia, N. Arkivoc 2002, (iii), 172.
• Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed., 2000,39,3773-3789.
• Davis, J. H. Jr. in Ionic Liquids in Synthesis; Wasserscheid,P.; Welton, T. (Eds.); Wiley-VCH: Weinheim, 1st ed., 2003,p. 33.
• Vaultier, M.; Kirschning, A.; Singh, V. in Ionic Liquids inSynthesis, Wasserscheid, P.; Welton, T. (Eds.); Wiley-VCH:Weinheim, 2nd ed., 2008; Vol. 2. p. 488.
• Fraga-Dubreuil, J.; Famelart, M. H.; Bazureau, J. P. OrganicProcess Research & Development 2002, 6, 374.
• Legeay, J. C.; Eynde, J. J. V.; Toupet, L.; Bazureau, J. P.Arkivoc 2007, (iii), 13.
• S. S. Khan, S. Hanelt, J. Liebscher, ARKIVOC 2009 (xii) 193-208.
• Giguere, R. J.; Bray, T. L.; Duncan, S. M.; Majetich,G.Tetrahedron Lett. 1986, 27, 4945-4948. b) Gedye, R.;Smith, F., Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.;Rousell, J.Tetrahedron Lett. 1986, 27, 279-282. c)Loupy, A.;Petit, A.; Hamelin, J.; Texier-Boullet, F.;Jacquault, P.; Mathé,D. Synthesis 1998, 1213-1234. d) Varma, R. S. Green Chem.1999, 43-48. c) Kidwai, M. Pure Appl.Chem. 2001, 73, 147-151. d) Varma, R. S. Pure Appl. Chem. 2001, 73, 193-198.
• a) Zhao, H.; Malhotra, V. Aldrichimica Acta, 2002, 35, 75-83.b) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust.J. Chem., 2004, 57, 113-119. c) Scammells, P. J.; Scott, J.A.;Singer, R. D. Aust. J. Chem., 2005, 158, 155-169.
• Karkkainen, J.; Asikkala, J.; Laitinen, R. S.; Lajunen, M. K.Z.Naturforsch. B 2004, 59, 763-770.
• a) Levenque, J. M.; Cravotto, G. Chimia 2006, 60, 613-620.b) R. M. Palou, J. Mex. Chem. Soc. 2007, 51(4), 252-264.
• a) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem.Rev. 2007, 107, 5471.b) A. Erkkilae, I. Majander, P. M. Pihko,Chem. Rev. 2007, 107, 5416.
• a) B. List, R. A. Lerner, C. F. Barbas, III, J. Am. Chem. Soc.2000, 122, 2395.b) G. Guillena, C. Najera, D. J. Ramon,Tetrahedron: Asymmetry 2007, 18, 2249.
• a) Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima,M. Shoji, Angew Chem Int Ed 2006, 45, 958. b) J.- C.Alexander, M. S. David, A. L. Deborah, B. G. Johan, V. L.Steven, Org. Biomol. Chem. 2005, 3, 84.
• M. Gruttadauria, F. Giacalone, R. Noto, Chem. Soc. Rev.,2008, 37, 1666–1688.

Identifiers

DOI

10.2478/asorg-2012-0002