Recent developments on task specific ionic liquids

Current Organic Chemistry

Volumn 15, Issue 8, 2011, Pages 1239-1248

  Chaturvedi, Devdutt ^a  

^a CSIR NORTH EAST INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

Author keywords

Chiral ionic liquids; Green reaction media; Ionic liquids; Task specific ionic liquids

Indexed keywords

STEREOCHEMISTRY;

BIOLOGICAL PROPERTIES; CHEMICAL AND BIOLOGICALS; CHIRAL IONIC LIQUIDS; GREEN REACTION MEDIUM; LIQUID COMPOSITIONS; ORGANIC SYNTHESIS; PHYSICAL-CHEMICAL PROPERTIES; TASK-SPECIFIC IONIC LIQUIDS; USER NEED;

IONIC LIQUIDS;

EID: 79953300742     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211795202997     Document Type: Review

References (59)

1. Welton T. Room temperature ionic liquids: Solvents for synthesis and catalysis. Chem. Rev., 1999, 99, 2071-2084.
2. Gorden, J. E. Techniques and methods of organic and organometallic chemistry; Dekker, New York, NY. 1969, 1, 51-188.
3. Wilkes, J.; Levisky, J.; Wilson, R.; Hussey, C. Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis. Inorg. Chem., 1982, 21, 1263-1364.
4. Wilkes, J. S. A short history of ionic liquids: from molten salts to neoteric solvents. Green Chem., 2002, 4, 73-80.
5. Boon, J. A.; Levisky, J. A.; Pflug, J. L.; Wilkes, J. S. Friedel-Craft reactions in ambient temperature molten salts. J. Org. Chem., 1986, 51, 480-483.
6. Earle, M. J.; Seddon, K. R. Ionic liquids: Green solvents for the future. Pure Appl. Chem., 2000, 72, 1391-1398.
7. Davis, Jr. J. H.; Forrester, K. J. Thiazolium-ion based organic ionic liquids (OILs). Novel OILs which promote the benzoin condensation. Tetrahedron Lett., 1999, 40, 1621-1622.
8. Davis Jr., J. H. Task specific ionic liquids. Chem. Lett., 2004, 3, 1072-1077.
9. Wierzbicki, A.; Davis, Jr. J. H. Proceedings of the Symposium on Advances in Solvent Selection and Substitution for Extraction, AIChE, New York, 2000.
10. 2 capture by a taskspecific ionic liquid. J. Am. Chem. Soc., 2002, 124, 926-927.
11. Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, Jr., J. H. Novel Bronsted acidic ionic liquids and their use as dual solvent-catalysts. J. Am. Chem. Soc., 2002, 124, 5962-5963.
12. S.-G. Functionalized imidazolium salts for task-specific ionic liquids and their applications. Chem. Commun., 2006, 1049-1063.
13. Winkel, A.; Reddy, P.V.G.; Wilhelm, R. Recent advances in the synthesis and application of chiral ionic liquids. Synthesis, 2008, 999-1016.
14. Uzagare, M. C.; Sanghvi, Y. S.; Salunkhe, M. M. Application of ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate in nucleoside chemistry. Green Chem., 2003, 5, 370-372.
15. Ranu, B. C.; Banerjee, S. Ionic liquid as a catalyst and reaction medium: The dramatic influence of a task specific ionic liquid, [Bmim]OH in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters and nitriles. Org. Lett., 2005, 7, 3049-3052.
16. Darvatkar, N. B.; Deorukhakar, A. R.; Bhilare, S. V.; Salunkhe, M. M. Ionic liquid mediated Knoevanagel condensation of Meldrum's acid and aldehydes. Synth. Commun., 2006, 36, 3043-3051.
17. Darvatkar, N. B., Deorukhkar, A. R., Bhilare, S. B., Raut, D. G.; Salukhe, M. M. Ionic liquid mediated synthesis of coumarin-3-carboxylic acid via Knoevanagel condensation of Meldrum's acid with ortho-hydroxy aryl aldehydes. Synth. Commun., 2008, 38, 3508-3513.
18. Dabiri, M.; Baghbanzadeh, M.; Delbari, A. S. Novel and efficient one-pot tandem synthesis of 2-styryl substituted 4(3H)-quinazolinones. J. Comb. Chem., 2008, 10, 700-703.
19. Hanelt, H.; Liebscher, J. A novel and versatile access to task specific ionic liquids based on 1,2,3-triazolium salts. Syn. Lett., 2008, 1058-1060.
20. Shinde, S. S.; Lee, B. S.; Chi, D.Y. Synergistic effects of two solvents, tert. alcohol and ionic liquid, in one molecule in nucleophilic fluorination. Org. Lett., 2008, 10, 733-735.
21. Yavari, I.; Kowsari, E. Task specific ionic liquid: A reusable and green catalyst for one-pot synthesis of highly functionalized pyrroles in aqueous media. Synlett., 2008, 897-899.
22. Zhang, Z.; Xie, Y.; Li, W.; Hu, S.; Song, J.; Jiang, T.; Han, B. Hydrogenation of carbon dioxide is promoted by task specific ionic liquid. Angew. Chem. Int. Ed., 2008, 47, 1127-1129.
23. Pavlinac, J.; Zupan, M.; Laali, K. K.; Stavber, S. Halogenation of organic compounds in ionic liquids. Tetrahedron, 2009, 65, 5625-5662.
24. Wang, L.; Li, H.; Li, P. Task specific ionic liquid as a base, ligand and reaction medium for the palladium catalyzed Heck reaction. Tetrahedron, 2009, 65, 364-368.
25. Bellina, F.; Bertoli, A.; Melai, B.; Scalesse, F.; Signori, F.; Chiappe, C. Synthesis and properties of glycerylimidazolium based ionic liquids: A promising class of task specific ionic liquids. Green Chem., 2009, 11, 622-629.
26. Park, B. Y.; Ryu, K. Y.; Park, J. H.; Lee, S. A dream combination for catalysis: Highly reactive and recyclable scandium (III) triflate-catalyzed cyanosilylations of carbonyl compounds in ionic liquids. Green Chem., 2009, 11, 946-948.
27. Wang Y.; Jiang, D.; Dai, L. Novel Brønsted acidic ionic liquids based on benzimidazolium cation: Synthesis and catalyzed acetalization of aromatic aldehydes with diols. Catal. Commun., 2008, 9, 2475-2480.
28. Leng, Y.; Wang, J.; Zhu, D.; Ren, X.; Ge, H.; Shin, L. Heteropolyanion based ionic liquids: Reaction induced self separation catalysts for esterification. Angew. Chem. Int. Ed., 2009, 48, 168-171.
29. Manhert, C. P.; Cook, R. A.; Dispenziere, Afeworkie, M. Supported ionic liquid catalysis: A new concept for homogeneous hydroformylation catalysis. J. Am. Chem. Soc., 2002, 124, 12932-12933.
30. Manhert, C. P.; Cook, R A.; Mozeleski, E. J. Supported ionic liquid catalysis investigated for hydrogenation reactions. Chem. Commun., 2002, 3010-3011.
31. Riisager, A.; Eriksen, K. M.; Wasserscheild, P.; Fehrmann, R. Propene and 1-octene hydroformylation with silica-supported, ionic liquid-phase (SILP) Rh-phosphine catalysts in continuous fixed-bed mode. Catal. Lett., 2003, 90, 149-153.
32. Riisager, A.; Eriksen, K. M.; Wasserscheild, P.; van Hal, R.; Fehrmann, R. Continuous fixed-bed gas-phase hydroformylation using supported ionic liquid-phase (SILP) Rh catalysts. J. Catal., 2003, 219, 452-455.
33. Gu, Y.; Ogawa, C.; Kobayashi, S. Silica-supported sodium sulfonate with ionic liquid: A neutral catalyst system for Michael reactions of indoles in water. Org. Lett., 2007, 9, 175-178.
34. Gu, Y.; Karam, A.; Jerome, F.; Barrault, J. Selectivity enhancement of silicasupported sulfonic acid catalysts in water by coating of ionic liquid. Org. Lett., 2007, 9, 3145-3148.
35. Astruc, D.; Lu, F.; Aranzaes, J. R. Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed., 2005, 44, 7852-7872.
36. Pachón, L. D.; Rothenberg, G. Transition metal nanoparticles: Synthesis, stability, and the leaching issue. Applied Organometal. Chem., 2008, 22, 288-299.
37. Gu, Y.; Li, G. Ionic liquids based catalysis with solids: State of art. Adv. Synth. Catal., 2009, 351, 817-847.
38. Redel, E.; Krämer, J.; Thomann, R.; Janiak, C. Synthesis of Co, Rh and Ir nanoparticles from metal carbonyls in ionic liquids and their use as biphasic liquid-liquid hydrogenation nanocatalysts for cyclohexene. J. Organometal. Chem., 2009, 694, 1069-1075.
39. Calo, V.; Nacci, A.; Monopoli, A.; Cotugno, P. Palladium nanoparticle catalyzed Ullmann reactions in ionic liquids with aldehydes as a reductants. Scope and mechanism Chem. Eur. J., 2009, 15, 1272-1279.
40. Taher, T.; Kim, J. B.; Jung, J. Y.; Ahn, W. S.; Jin, M. J. Highly active and magnetically recoverable Pd-NHC catalyst immobilized on Fe3O4 nanoparticle-ionic liquid matrix for Suzuki reaction in water. Synlett., 2009, 15, 2477-2482.
41. Raut, D. G., Wankhede, K. S.; Vaidya, V. V.; Bhilare, S. V.; Darvatkar, N. B.; Deorukhkar, A. R.; Trivedi, G. K.; Salunkhe, M. M. Copper nanoparticles in ionic liquids: Recyclable and efficient catalytic system for 1,3-dipolar cycloaddition reaction. Catal. Commun., 2009, 10, 1240-1243.
42. Dupont, J.; Suarez, P. A. Z.; de Souza, R. F.; Burrow, R. A.; Kintzinger, J. P. CH-_ interactions in 1-n-butyl-3-methylimidazolium tetraphenylborate molten salt: Solid and solution structure. Chem. Eur. J., 2000, 6, 2377-2381.
43. Hagiwara, R.; Ito, Y. Room temperature ionic liquids of alkylimidazolium cations and fluoroanions. J. Fluorine Chem., 2000, 105, 221-227.
44. Schröder, U.; Wadhawan, J. D.; Compton, R. G.; Marken, F.; Suarez, P. A. Z.; Consorti, C. S.; de Souza, R. F.; Dupont, J. Water-induced accelerated ion diffusion: Voltammetric studies in 1-methyl-3-[2,6-(S)-dimethylocten-2-yl]imidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium tetrafluoroborate and hexafluorophosphate ionic liquids. New J. Chem., 2000, 24, 1009-1015.
45. Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, 2003.
46. Ding, J.; Armstrong, D. W. Chiral ionic liquids: Synthesis and applications. Chirality, 2005, 17, 281-292.
47. Baudequin, C.; Bregeon, D.; Levillain, J.; Guillen, F.; Plaquevent, J. C.; Gaumont, A. C. Chiral ionic liquids, a renewal for the chemistry of chiral solvents: Design, synthesis and applications for chiral recognition and asymmetric synthesis. Tetrahedron: Asymm., 2005, 16, 3921-3945.
48. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Diels-Alder reactions in ionic liquids. Green Chem., 1999, 1, 23-25.
49. Bonanni, M.; Soldaini, G.; Faggi, C.; Goti, A.; Cardona, F. Novel L-tartaric acid derived pyrrolidinium cations for the synthesis of chiral ionic liquids. Synlett, 2009, 747-750.
50. Siyutkin, D. E.; Kucherenko, A. S.; Struchkova, M. I.; Zlotin, S. G. A novel (S) -proline modified task specific chiral ionic liquid-an amphiphilic recoverable catalyst for direct asymmetric aldol reactions in water. Tetrahedron Lett., 2008, 49, 1212-1216.
51. Li, J.; Hu, F.; Xie, X.; Liu, F.; Huang, Z. Synthesis of new funtionalized chiral ionic liquid and its organocatalytic asymmetric epoxidation in water. Catal. Commun., 2009, 11, 276-279.
52. Li, M.; Gardella, J.; Bwambok, D.; El-Zahab, B.; Rooy, S.; Cole, M.; Lowry, M.; Warner, I. Combinatorial approaches to enatiomeric discrimination: Synthesis and 19F NMR screening of chiral ionic liquid-modified silane library. J. Comb. Chem., 2009, 11, 1105-1114.
53. 2 to epoxides. Green Chem., 2009, 11, 935-938.
54. Tan, R.; Yin, D.; Yu, N.; Zhao, H.; Yina, D. Easily recyclable polymeric ionic liquid functionalized chiral salen Mn (III) complex for enatioselective epoxidation of styrene. J. Catal., 2009, 263, 284-291.
55. Miao, T.; Wang, L.; Li, P.; Yan, J. A highly efficient and recyclable ionic liquid anchored pyrrolidine catalyst for enatioselective Michael additions. Synthesis, 2008, 23, 3828-3834.
56. Van Buu O. N.; Aupoix, A.; Vo-Thanh, G. Synthesis of novel chiral imidazolium- based ionic liquid derived from isosorbide and their applications in asymmetric aza Diels-Alder reaction. Tetrahedron, 2009, 65, 2260-2265.
57. Plaza, P. G. J.; Bhongade, B A.; Singh, G. Synthesis of chiral carbohydrate ionic liquids. Synlett, 2008, 2973-2976.
58. Nageshwar, D.; Rao, D. M.; Acharyulu, V. R. P. Terpenes to ionic liquids: Synthesis and characterization of citronellal based chiral ionic liquids. Synth. Commun. 2009, 39, 3357-3368.
59. Glushkov, V. A.; Kotelev, M. S.; Rudovskii, K. S.; Maiorova, O. A.; Tarantin, A. V.; Tolstikov, A. G. Chiral ionic liquids based on abietane. Russ. J. Org. Chem., 2009, 45, 404-409.