Applications of ionic liquids in organic synthesis and catalysis

Clean Technologies and Environmental Policy

Volumn 16, Issue 8, 2014, Pages 1487-1513

  Qureshi, Ziyauddin S ^a   Deshmukh, Krishna M ^a   Bhanage, Bhalchandra M ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Catalysis; Ionic liquids; Organic synthesis

Indexed keywords

CATALYSTS; IONIC LIQUIDS; PILOT PLANTS;

CATALYTIC REACTIONS; IONIC LIQUID (ILS); MOLECULAR SOLVENTS; ORGANIC SYNTHESIS; PILOT PLANT SCALE; PREPARATION METHOD; REACTION PROCESS;

CATALYSIS;

EID: 84920710529     PISSN: 1618954X     EISSN: 16189558     Source Type: Journal    
DOI: 10.1007/s10098-013-0660-0     Document Type: Article

References (149)

1. Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2002) Quaternary ammonium zinc- or tin-containing ionic liquids: water insensitive, recyclable catalysts for Diels-Alder reactions. Green Chem 4:24-26
2. Abu-Reziq R, Wang D, Post M, Alper H (2007) Platinum nanoparticles supported on ionic liquid-modified magnetic nanoparticles: selective hydrogenation catalysts. Adv Synth Catal 349:2145-2150
3. Akbari J, Heydari A, Kalhor HR, Kohan SA (2010) Sulfonic acid functionalized ionic liquid in combinatorial approach, a recyclable and water tolerant-acidic catalyst for one-pot Friedlander quinoline synthesis. J Comb Chem 12:137-140
4. Arduengo AJ (1999) Looking for stable carbenes: the difficulty in starting A new. Acc Chem Res 32:913-921
5. Arhancet JP, Davis DE, Merola JS, Hanson BE (1989) Hydroformylation by supported aqueous-phase catalysis: a new class of heterogeneous catalysts. Nature 339:454-455
6. Axens (2007) Dimersol-X. http://www.axens.net/html-gb/offer/offer-processes-70.html.php
7. Baker J (2004) ECN Innovation Awards 2004 - the winners! Eur Chem News 18-19
8. BASF (2005a) Acid scavenging: the BASIL process. http://www2.basf.de/en/intermed/nbd/products/ionic-liquids/processes/acid.htm?id=mGwEvAf1Ebw23hM
9. BASF (2005b) Chlorination with nucleophilic HCl. http://www2.basf.de/en/intermed/nbd/products/ionic-liquids/processes/chlorination.htm?id=mGwEvAf1Ebw23hM
10. Beletskaya IP, Cheprakov AV (2000) The Heck reaction as a sharpening stone of palladium catalysis. Chem Rev 100:3009-3066
11. Bo W, Ming YL, Shaun SJ (2003) Ionic liquid-regulated sulfamic acid: chemoselective catalyst for the transesterification of β-ketoesters. Tetrahedron Lett 44:5037-5039
12. Boon JA, Levisky JA, Pflug JL, Wilkes JS (1986) Friedel-Crafts reactions in ambient-temperature molten salts. J Org Chem 51:480-483
13. Central Glass Co. (Japan) (2007). http://www.cgco.co.jp/english/index.html
14. Chauvin Y, Gaillard JF, Quang DV, Andrews JW (1974) The IFP Dimersol process for dimerization of C3 and C4 olefinic cuts. Chem Ind 375-378
15. Chauvin Y, Gilbert B, Guibard I (1990) Catalytic dimerization of alkenes by nickel complexes in organochloroaluminate molten salts. J Chem Soc Chem Commun 1715-1716
16. Chauvin Y, Hirschauer A, Olivier H (1994) Alkylation of isobutane with 2-butene using 1-butyl-3-methylimidazolium chloride-aluminium chloride molten salts as catalysts. J Mol Catal 92:155-165
17. 3-x (x = 0, 1) ionic liquids. Ind Eng Chem Res 34:1149-1155
18. Chauvin Y, Mussmann L, Olivier H (1995b) A novel class of versatile solvents for two-phase catalysis: hydrogenation, isomerization, and hydroformylation of alkenes catalyzed by rhodium complexes in liquid 1,3-dialkylimidazolium salt. Angew Chem Int Ed Engl 34:2698-2700
19. Chauvin Y (2006) Olefin Metathesis: the early days (Nobel Lecture). Angew Chem Int Ed 45:3740-3747
20. Chen W, Zhang Y, Zhu L, Lan J, Xie R, You J (2007) A concept of supported amino acid ionic liquids and their application in metal scavenging and heterogeneous catalysis. J Am Chem Soc 129:13879-13886
21. Cole AC, Jensen JL, Ntai I, Tran KLT, Weaver KJ, Forbes DC, Davis JH Jr (2002) Novel Brønsted acidic ionic liquids and their use as dual solvent-catalysts. J Am Chem Soc 124:5962-5963
22. Cull SG, Holbrey JD, Vargas-Mora V, Seddon KR, Lye GJ (2000) Room-temperature ionic liquids as replacements for organic solvents in multiphase bioprocess operations. Biotechnol Bioeng 69:227-233
23. De Bellefon C, Pollet E, Grenouillet P (1999) Molten salts (ionic liquids) to improve the activity, selectivity and stability of the palladium catalysed Trost-Tsuji C-C coupling in biphasic media. J Mol Catal A Chem 145:121-126
24. De Munck NA, Verbruggen MW, De Leur JE, Scholten JJF (1981) Gas phase hydroformylation of propylene with porous resin anchored rhodium complexes part II. The catalytic performance. J Mol Catal 331-342
25. Deshmukh KM, Qureshi ZS, Nandurkar NS, Bhanage BM (2009) One-pot synthesis of β-amido ketones using Bronsted acidic ionic liquid as an efficient and reusable catalyst. Can J Chem 81:401-405
26. Deshmukh KM, Qureshi ZS, Dhake KP, Bhanage BM (2010) Transesterification of dimethyl carbonate with phenol using Brønsted and Lewis acidic ionic liquids. Catal Commun 12:207-211
27. -: an efficient and recyclable catalyst for the synthesis of 1-amidoalkyl-2-naphthols and 1-carbamatoalkyl-2-naphthols under solvent free conditions. Synth Commun 42:93-101
28. 6)] as a reaction medium. Tetrahedron Lett 50:2811-2814
29. Dong F, Jun L, Xinli Z, Zhiwen Y, Zuliang L (2007) One-pot green procedure for Biginelli reaction catalyzed by novel task-specific room-temperature ionic liquids. J Mol Catal A Chem 274:208-211
30. Dong F, Zhenghao F, Zuliang L (2009) Functionalized ionic liquid as the recyclable catalyst for Mannich-type reaction in aqueous media. Catal Commun 10:1267-1270
31. Du Y, Tian F (2005) Brønsted acidic ionic liquids as efficient and recyclable catalysts for protection of carbonyls to acetals and ketals under mild conditions. Syn Commun 35:2703-2708
32. 2) catalyzed protection of carbonyls at room temperature under solvent-free conditions. Catal Commun 7:651-656
33. Duan Z, Gu Y, Zhang J, Zhu L, Deng Y (2006b) Protic pyridinium ionic liquids: synthesis, acidity determination and their performances for acid catalysis. J Mol Catal A Chem 250:163-168
34. Dullius JEL, Suarez PAZ, Einloft S, De Souza RF, Dupont J, Fischer J, De Cian A (1998) Selective catalytic hydrodimerization of 1,3-butadiene by palladium compounds dissolved in ionic liquids. Organometallics 17:815-819
35. Earle MJ, Seddon KR, Adams CJ, Roberts GC (1998) Friedel-Crafts reactions in room temperature ionic liquids. Chem Commun 2097-2098
36. Earle MJ, Seddon KR, McCormac PB (2000) The first high yield green route to a pharmaceutical in a room temperature ionic liquid. Green Chem 2:261-262
37. Earle MJ, Katdare SP, Seddon KR (2004) Paradigm confirmed: the first use of ionic liquids to dramatically influence the outcome of chemical reactions. Org Lett 6:707-710
38. Erbeldinger M, Mesiano AJ, Russell J (2000) Enzymatic catalysis of formation of Z-aspartame in ionic liquid-an alternative to enzymatic catalysis in organic solvents. Biotechnol Progr 16:1129-1131
39. Fadeev AG, Meagher MM (2001) Opportunities for ionic liquids in recovery of biofuels. Chem Commun 3:295-296
40. Favre F, Forestiere A, Hugues F, Olivier-Bourbigou H, Chodorge JA (2005) Butenes dimerisation: from monophasic dimersol™ to biphasic difasol™. Oil Gas Eur Mag 31:83-87
41. Fei Z, Zhao D, Geldbach TJ, Scopelliti R, Dyson PJ (2004) Brønsted acidic ionic liquids and their zwitterions: synthesis, characterization and pKa determination. Chem Eur J 10:4886-4893
42. Fried J, Lin C, Mehra M, Kao W, Dalven P (1971) Synthesis and biological activity of prostaglandins and prostaglandin antagonists. Ann N Y Acad Sci 180:38-63
43. Fukuyama T, Shinmen M, Nishitani S, Sato M, Ryu I (2002) A copper-free Sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling. Org Lett 4:1691-1694
44. Gong K, Fang D, Wang H-L, Liu Z-L (2007) Basic functionalized ionic liquid catalyzed one-pot Mannich-type reaction: three component synthesis of β-amino carbonyl compounds. Monatsh Fur Chem 138:1195-1198
45. Gordon CM (2001) New developments in catalysis using ionic liquids. App Catal A Gen 222:101-117
46. Green MJ (2004) Ionic liquids: a road-map to commercialisation. Royal Society of Chemistry, London
47. Grubbs RH (2003) Handbook of metathesis. Wiley, Weinheim
48. Hajipour AR, Rafiee F (2010) Acidic Bronsted ionic liquids. Org Prep Proc Int 42:285-362
49. Haumann M, Riisager A (2008) Hydroformylation in room temperature ionic liquids (RTILs): catalyst and process developments. Chem Rev 108:1474-1497
50. Hjortkjaer J, Heinrich B, Capka M (1990) Influence of the ligand structure on SLP-catalysed hydroformylation of propene. Appl Organomet Chem 4:369-374
51. 6. Tetrahedron Lett 41:6627-6629
52. IFP (2004) Annual Report
53. 6]. J Chem Res 6:370-372
54. Johnson WS, Brinkmeyer RS, Kapoor UM, Yarnell TL (1977) Asymmetric total synthesis of 11.alpha.-hydroxyprogesterone via a biomimetic polyene cyclization. J Am Chem Soc 99:8341-8343
55. Johnson KE, Pagni RM, Bartmess J (2007) Brønsted acids in ionic liquids: fundamentals, organic reactions, and comparisons. Monatsh Fur Chem 138:1077-1101
56. Joni J, Haumann M, Wasserscheid P (2009) Development of a supported ionic liquid phase (SILP) catalyst for slurry-phase Friedel-Crafts alkylations of cumene. Adv Synth Catal 351:423-431
57. Karthikeyan G, Perumal PT (2004) A mild, efficient and improved protocol for the friedlander synthesis of quinolines using lewis acidic ionic liquid. J Heterocycl Chem 41:1039-1041
58. Kaufmann DE, Nouroozian M, Henze H (1996) Molten salts as an efficient medium for palladium catalyzed C-C coupling reactions. Synlett 1091-1092
59. Kishi Y, Inagi S, Fuchigami T (2008) Facile and highly efficient synthesis of fluorinated heterocycles via Prins cyclization in ionic liquid hydrogen fluoride salts. Chem Commun 3876-3878
60. Kmentova I, Gotov B, Gajda V, Toma S (2003) The Sonogashira reaction in ionic liquids. Monatsh Chem 134:545-549
61. Knifton JF (1987) Syngas reactions: part XI. The ruthenium 'melt' catalyzed oxonation of internal olefins. J Mol Catal 43:65-77
62. Knifton JF (1988) Syngas reactions: part XIII. The ruthenium 'melt'-catalyzed oxonation of terminal olefins. J Mol Catal 47:99-116
63. Kumar A, Pawar SS (2004) Converting exo-selective Diels-Alder reaction to endo-selective in chloroloaluminate ionic liquids 69:1419-1420
64. Kumar A, Pawar SS (2005) Catalyzing Henry reactions in chloroaluminate ionic liquids. J Mol Catal A Chem 235:244-248
65. Lee CW (1999) Diels-Alder reactions in chloroaluminate ionic liquids: acceleration and selectivity enhancement. Tetrahedron Lett 40:2461-2464
66. 3H-functionalized Brønsted acidic ionic liquids. Ultrason Sonochem 17:752-755
67. 3H functionalized ionic liquid and its catalytic activities for biodiesel synthesis. Green Chem 12:201-204
68. Liu Y, Wang S-S, Liu W, Wan Q-X, Wu H-H, Gao G-H (2009) Transition-metal catalyzed carbon-carbon couplings mediated with functionalized ionic liquids, supported-ionic liquid phase, or ionic liquid media. Curr Org Chem 13:1322-1346
69. Maase M, Massonne K, Halbritter K, Noe R, Bartsch M, Siegel W, Stegmann V, Flores M, Huttenloch O Becker M. (2003) Method for the separation of acids from chemical reaction mixtures by means of ionic fluids, World Patent, WO 2003 062171
70. Madeira Lau R, Van Rantwijk F, Seddon KR, Sheldon RA (2000) Lipase-catalyzed reactions in ionic liquids. Org Lett 2:4189
71. Magnuson DK, Bodley JW, Evans DF (1984) The activity and stability of alkaline phosphatase in solutions of water and the fused salt ethylammonium nitrate. J Sol Chem 13:583-587
72. Malhotra SV (2007) Ionic liquids in organic synthesis, ACS Symposium, vol 950. Oxford University Press, New York
73. Mehnert CP, Cook RA, Dispenziere NC, Afeworki MJ (2002) Supported ionic liquid catalysis - a new concept for homogeneous hydroformylation catalysis. J Am Chem Soc 124:12932-12933
74. Mizushima E, Hayashi T, Tanaka M (2001) Palladium-catalysed carbonylation of aryl halides in ionic liquid media: high catalyst stability and significant rate-enhancement in alkoxycarbonylation. Green Chem 3:76-79
75. Monteiro AL, Zinn FK, De Souza RF, Dupont J (1997) Asymmetric hydrogenation of 2-arylacrylic acids catalyzed by immobilized Ru-BINAP complex in 1-n-butyl-3-methylimidazolium tetrafluoroborate molten salt. Tetrahedron Asymmetry 8:177-179
76. 2 with product isolation by direct sublimation from the ionic liquid. Chem Commun 158-159
77. Nageshwar Rao I, Prabhakaran EN, Das SK, Iqbal J (2003) Cobalt-catalyzed one-pot three-component coupling route to β-acetamido carbonyl compounds: a general synthetic protocol for γ-lactams. J Org Chem 68:4079-4082
78. Naik PU, Harjani JR, Nara SJ, Salunkhe MM (2004) Ionic liquid enabled sulfamoylation of arenes: an ambient, expeditious and regioselective protocol for aryl sulfonamides. Tetrahedron Lett 45:1933-1936
79. Nara SJ, Harjani JR, Salunkhe MM (2001) Friedel-Crafts sulfonylation in 1-butyl-3-methylimidazolium chloroaluminate ionic liquids. J Org Chem 66:8616-8620
80. Nobel Foundation (2007) The Nobel Prize in Chemistry 2005. http://nobelprize.org/nobel-prizes/chemistry/laureates/2005/index.html
81. Olivier-Bourbigou H, Hugues F (2002) Green industrial applications of ionic liquids. In: Rogers RD, Seddon KR, Volkov S (eds) NATO science series II: mathematics, physics and chemistry, vol 92. Kluwer, Dordrecht, pp 67-84
82. Olivier-Bourbigou H, Lecocq V (2002) Science and technology in catalysis, In: Studies in surface science and catalysis, vol 145. Kodansha Ltd., Tokyo, pp 55-60
83. Owens GS, Abu-Omar MM (2000) Methyltrioxorhenium-catalyzed epoxidations in ionic liquids. Chem Commun 1165-1166
84. Palimkar SS, Siddiqui SA, Daniel T, Lahoti RJ, Srinivasan KV (2003) Ionic liquid-promoted regiospecific Friedlander annulation: novel synthesis of quinolines and fused polycyclic quinolines. J Org Chem 68:9371-9378
85. 3-supported ionic liquid phase catalyst, followed by a novel route to pyrazolin-5-ones. App Catal A Gen 347:142-147
86. 3 supported ionic liquid-phase catalyst. Ind Eng Chem Res 47:969-972
87. Park SB, Alper H (2003) Recyclable Sonogashira coupling reactions in an ionic liquid, effected in the absence of both a copper salt and a phosphine. Chem Commun 1306-1307
88. Patil YP, Tambade PJ, Deshmukh KM, Bhanage BM (2009) Synthesis of quinazoline-2,4(1H,3H)-diones from carbon dioxide and 2-aminobenzonitriles using [Bmim]OH as a homogeneous recyclable catalyst. Catal Today 148:355-360
89. Plechkova NV, Seddon KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123-150
90. Qureshi ZS, Deshmukh KM, Bhor MD, Bhanage BM (2009) Bronsted acidic ionic liquid as an efficient and reusable catalyst for transesterification of β-ketoesters. Catal Commun 10:833-837
91. Qureshi ZS, Deshmukh KM, Tambade PJ, Bhanage BM (2010a) Amberlyst-15 in ionic liquid: an efficient and recyclable reagent for the benzylation and hydroalkylation of β-dicarbonyl compounds. Tetrahedron Lett 51:724-729
92. Qureshi ZS, Deshmukh KM, Tambade PJ, Dhake KP, Bhanage BM (2010) Amberlyst-15 in ionic liquid: an efficient and recyclable reagent for nucleophilic substitution of alcohols and hydroamination of alkenes. Eur J Org Chem 6233-6238
93. Qureshi ZS, Deshmukh KM, Dhake KP, Bhanage BM (2011) Brønsted acidic ionic liquid: a simple, efficient and recyclable catalyst for regioselective alkylation of phenols and anti-Markovnikov addition of thiols to alkenes. RSC Adv 1:1106-1112
94. Raed AR, Wang D, Post M, Alper H (2007) Platinum nanoparticles supported on ionic liquid-modified magnetic nanoparticles: selective hydrogenation catalysts. Adv Synth Catal 349:2145-2150
95. Rakita PE (2005) Opportunities for ionic liquid commercialization. AIChE Spring National Meeting, Conference Proceedings, pp 3451
96. Ranu BC, Banerjee S (2005) Ionic liquid as 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 7:3049-3052
97. Ranu BC, Jana R (2006) Ionic liquid as catalyst and reaction medium: a simple, efficient and green procedure for Knoevenagel condensation of aliphatic and aromatic carbonyl compounds using basic ionic liquid, [bmIm]OH. Eur J Org Chem 3767-3770
98. Ranu BC, Adak L, Banerjee S (2008) Ionic liquid promoted interrupted Feist-Benary reaction with high diastereoselectivity. Tetrahedron Lett 49:4613-4617
99. Ranwell A, Tshamano MA (2002) Ionic liquids: industrial applications to green chemistry. In: Rogers RD, Seddon KR (eds) ACS Symposium Series, vol 818. American Chemical Society, Washington DC, pp 147-161
100. Ranwell A, Dwyer CL, Ajam M (2004) Potential application of ionic liquids for olefin oligomerization. IP.com J 4:4
101. Rebeiro GL, Khadilkar BM (2001) Chloroaluminate ionic liquids for Fischer-Indole synthesis. Synthesis 3:370-372
102. 4 in a Brønsted acidic ionic liquid. Tetrahedron Lett 48:8807-8810
103. Riisager A, Eriksen KM, Wasserscheid P, Fehrmann R (2003a) Propene and 1-octene hydroformylation with silica-supported, ionic liquid-phase (SILP) Rh-phosphine catalysts in continuous fixed-bed mode. Catal Lett 90:149-153
104. Riisager A, Wasserscheid P, Van Hal R, Fehrmann R (2003b) Continuous fixed-bed gas-phase hydroformylation using supported ionic liquid-phase (SILP) Rh catalysts. J Catal 219:452-455
105. Riisager A, Fehrmann R, Flicker S, Van Hal R, Haumann M, Wasserscheid P (2005a) Very stable and highly regioselective supported ionic-liquid-phase (SILP) catalysis: continuous-flow fixed-bed hydroformylation of propene. Angew Chem Int Ed 44:815-819
106. Riisager A, Fehrmann R, Haumann M, Gorle BSK, Wasserscheid P (2005b) Stability and kinetic studies of supported ionic liquid phase catalysts for hydroformylation of propene. Ind Eng Chem Res 44:9853-9859
107. Ross L, Chen W, Xu L, Mao L (2001) Ligand effects in palladium-catalyzed Allylic alkylation in ionic liquids. Organometallics 20:138-142
108. Ryan TA, Ryan C, Seddon EA, Seddon KR (1996) In: Clark RJH (ed) Phosgene and related carbonyl halides, Elsevier, Amsterdam
109. 4] promoted synthesis of α-aminophosphonates. Bull Korean Chem Soc 30:1054-1056
110. Sahoo S, Joseph T, Halligudi SB (2006) Mannich reaction in Bronsted acidic ionic liquid: a facile synthesis of β-amino carbonyl compounds. J Mol Catal A Chem 244:179-182
111. Schmid CR, Beck CA, Cronin JS, Staszak MA (2004) Demethylation of 4-methoxyphenylbutyric acid using molten pyridinium hydrochloride on multikilogram scale. Org Process Res Dev 8:670-673
112. Seddon KR (1997) Ionic liquids for clean technology. J Chem Technol Biotechnol 68:351-356
113. 2 absorbing cost-effective ionic liquid for synthesis of commercially important alpha cyanoacrylic acids: a safe process for activation of cyanoacetic acid. Green Chem 11:526-530
114. Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 2399-2407
115. Silva SM, Suarez PAZ, De Souza RF, Dupont J (1998) Selective linear dimerization of 1,3-butadiene by palladium compounds immobilized into 1-n-butyl-3-methyl imidazolium ionic liquids. Polym Bull 40:401-405
116. Stark A, Seddon KR (2007) Ionic liquids, In: Kirk-Othmer Encyclopedia of Chemical Technology, vol 26. Wiley, New York, pp 836-920. doi: 10.1002/0471238961.ionisedd.a01
117. Stark A, Ajam M, Green M, Raubenheimer HG, Ranwell A, Ondruschka B (2006) Metathesis of 1-octene in ionic liquids and other solvents: effects of substrate solubility, solvent polarity and impurities. Adv Synth Catal 348:1934-1941
118. Stegmann V, Massonne K (2005) Method for producing haloalkanes from alcohols. WO Pat. 2005 026089
119. Sunitha S, Kanjilal S, Reddy PS, Prasad RBN (2008) An efficient and chemoselective Brønsted acidic ionic liquid-catalyzed N-Boc protection of amines. Tetrahedron Lett 49:2527-2532
120. Surette JKD, Green L, Singer RD, (1996) 1-Ethyl-3-methylimidazolium halogenoaluminate melts as reaction media for the Friedel-Crafts acylation of ferrocene. Chem Commun 2753-2754
121. Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose with ionic liquid. J Am Chem Soc 124:4974-4975
122. Tan SSY, MacFarlane DR (2010) Ionic liquids in biomass processing. In: Kirchner B (ed) Ionic liquids, trends in current chemistry, vol 290. Springer, New York, pp 311-339
123. Thomazeau C, Olivier-Bourbigou H, Magna L, Luts S, Gilbert B (2003) Determination of an acidic scale in room temperature ionic liquids. J Am Chem Soc 125:5264-5265
124. 6] ionic liquid. Green Chem 2:149-151
125. van Rantwijk F, Lau RM (2003) Biocatalytic transformations in ionic liquids. Trends Biotechnol 21:131-138
126. Walden P (1914) Ueber die Molekulargrösse und elektrische Leitfähigkeit einiger geschmolzenen salze. Bull Acad Imper Sci 8:405-422
127. Wang W, Shao L, Cheng W, Yang J, He M (2008) Brønsted acidic ionic liquids as novel catalysts for Prins reaction. Catal Commun 9:337-341
128. Wasserscheid P, Keim W (2000) Ionic liquids - new "solutions" for transition metal catalysis. Angew Chem Int Ed 39:3772-3789
129. Wasserscheid P, Welton T (2007) Ionic liquids in synthesis, 2nd edn. Wiley, Weinheim
130. Welton T (1999) Room-temperature ionic liquids. Solvent for synthesis and catalysis. Chem Rev 99:2071-2083
131. Wasserscheid P, Welton T (2003) Ionic liquids in synthesis. Wiley, Weinheim
132. Welton T (2004) Ionic liquids in catalysis. Coord Chem Rev 248:2459-2477
133. Williams DBG, Ajam M, Ranwell A (2006) Highly selective metathesis of 1-octene in ionic liquids. Organometallics 25:3088-3090
134. 4. Tetrahedron Lett 45:4963-4965
135. Wu Q, Chen H, Han M, Wang D, Wang J (2007) Transesterification of cottonseed oil catalyzed by Brønsted acidic ionic liquids. Ind Eng Chem Res 46:7955-7960
136. Wu H, Zhang FR, Wan Y, Ye L (2008) An efficient protocol for Henry reaction using basic ionic liquid [bmIm]OH as catalyst and reaction medium. Org Lett 5:209-211
137. Xing H, Wang T, Zhou Z, Dai Y (2005) Novel Brønsted-acidic ionic liquids for esterifications. Ind Eng Chem Res 44:4147-4150
138. Xu J-M, Liu B-K, Wu W-B, Qian C, Wu Q, Lin X-F (2006) Basic ionic liquid as catalysis and reaction medium: a novel and green protocol for the Markovnikov addition of N-heterocycles to vinyl esters, using a task-specific ionic liquid, [bmIm]OH. J Org Chem 71:3991-3993
139. Yadav LDS, Rai A, Rai VK, Awasthi C (2008) Chiral ionic liquid-catalyzed Biginelli reaction: stereoselective synthesis of polyfunctionalized perhydropyrimidines. Tetrahedron 64:1420-1429
140. Yang Y-L, Kou Y (2004) Determination of the Lewis acidity of ionic liquids by means of an IR spectroscopic probe. Chem Commun 226-227
141. Yang Y, Deng C, Yuan Y (2005) Characterization and hydroformylation performance of mesoporous MCM-41-supported water-soluble Rh complex dissolved in ionic liquids. J Catal 232:108-116
142. Zhao H, Malhotra SV (2002) Applications of ionic liquids in organic synthesis. Aldrichim Acta 35:75-83
143. Zhao D, Wu M, Kou Y, Min E (2002) Ionic liquids: applications in catalysis. Today 74:157-189
144. Zhao G, Jiang T, Gao H, Han B, Huang J, Sun D (2004) Mannich reaction using acidic ionic liquids as catalysts and solvents. Green Chem 6:75-77
145. Zhao H, Song Z, Olubajo O, Cowins JV (2010) New ether-functionalized ionic liquids for lipase-catalyzed synthesis of biodiesel. Appl Biochem Biotechnol 162:13-23
146. Zheng X, Qian Y-B, Wang Y (2010) 2-Pyrrolidinecarboxylic acid ionic liquid as a highly efficient organocatalyst for the asymmetric one-pot Mannich reaction. Eur J Org Chem 515-522
147. Zhu H-P, Yang F, Tang J, He M-Y (2003) Brønsted acidic ionic liquid 1-methylimidazolium tetrafluoroborate: a green catalyst and recyclable medium for esterification. Green Chem 5:38-39
148. Zhu S, Wu Y, Chen Q, Yu Z, Wang C, Jin S, Ding Y, Wu G (2006) Dissolution of cellulose with ionic liquids and its application: a mini-review. Green Chem 8:325-327
149. Zim D, De Souza RF, Dupont J, Monteiro AL (1998) Regioselective synthesis of 2-arylpropionic esters by palladium-catalyzed hydroesterification of styrene derivatives in molten salt media. Tetrahedron Lett 39:7071-7074