Green solvents in organic synthesis: An overview

Current Organic Chemistry

Volumn 17, Issue 11, 2013, Pages 1179-1187

  Shanab, Karem ^a   Neudorfer, Cathanna ^a   Schirmer, Eva ^a   Spreitzer, Helmut ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Alternative solvents; Carbonates; Fluorous solvents; Green chemistry; Green solvents; Ionic liquids; Solvents; Supercritical carbon dioxide

Indexed keywords

CARBON DIOXIDE; CARBONATES; IONIC LIQUIDS; SUPERCRITICAL FLUID EXTRACTION;

ALTERNATIVE SOLVENTS; ENVIRONMENTAL DAMAGE; FLUOROUS SOLVENTS; GREEN-CHEMISTRY; GREENER SOLVENTS; ORGANIC CHEMISTRY; ORGANIC SYNTHESIS; SOLVENT FREE PROCESS; SUPERCRITICAL CARBONDIOXIDES; TOXIC SOLVENTS;

SOLVENTS;

EID: 84881328956     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272811317110005     Document Type: Article

References (72)

1. DeSimone, J. Practical Approaches to Green Solvents. Science, 2002, 297, 799-803.
2. Horvàth, I. T. Fluorous Biphase Chemistry. Acc. Chem. Res., 1998, 31, 641-650.
3. Taverner, S. J.; Clark, J. H. Can fluorine chemistry be green chemistry? J. Fluorine Chem., 2003, 123, 31-36.
4. Sheldon, R.A. Green solvents for sustainable organic synthesis: state of the art. Green Chem., 2005, 7, 267-278.
5. Suresh; Sandhu, J.S. Recent Advances in Ionic Liquids. Green unconventional Solvents of this Century. Part 1. Green Chem. Lett. Rev., 2011, 4, 289-310.
6. Orha, L.; Akien, G. R.; Horvath, I. T. In: Handbook of Green Chemistry; Wiley: 2012; Vol 7, pp. 93-120.
7. Jessop, P.G. Searching for Green Solvents. Green Chem., 2011, 13, 1391-1398.
8. Cornils, B.; Wiebus, E. Virtually no environmental impact: The biphasic oxo process. Recl. Trav. Chim. Pays-Bas, 1996, 115, 211-215.
9. Kuntz, E.G. Homogeneous catalysis in water. CHEMTECH, 1987, 17, 570-575.
10. Joo, F.; Toth, Z. Catalysis by water-soluble phosphine complexes of transition metal ions in aqueous and two-phase media. J. Mol. Catal., 1980, 8, 369-383.
11. Takashi, S.; Dakka, J.; Sheldon, R. A. Titanium-substituted zeolite beta(Ti-Al-AA)-catalysed epoxidation of oct-1-ene with tert-butyl hydroperoxide(TBHP). J. Chem. Soc., Chem. Commun., 1994, 1887-1888.
12. Papadogianakis, L.M.; Sheldon, R.A. Catalytic conversions in water. Part 5: Carbonylation of 1-(4-iso-butylphenyl)ethanol to ibuprofen catalyzed by water-soluble palladium-phosphine complexes in a two-phase system. J. Chem. Technol. Biotechnol., 1997, 70, 83-91.
13. Ten Brink, G.J.; Arends, I.W.; Sheldon, R.A. Green, catalytic oxidation of alcohols in water. Science, 2000, 287, 1636-1639.
14. Gorke, J.; Romas, S.; Kazlauskas, R. Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis. Biotechnology and Bioprocess Engineering, 2010, 1, 40-53.
15. Wegman, M.A.; Janssen, H.A.; van Rantwijk, F.; Sheldon, R.A. Towards biocatalytic synthesis of Î-lactam antibiotics. Adv. Synth. Catal., 2001, 343, 559-576.
16. Oyama, K. In: Chirality in Industry; Collins, Sheldrake, Crosby, Eds.; Wiley & Sons: NY, 1992; pp. 237-248.
17. Gavagan, J.E.; Fager, S.K.; Seip, J.E.; Payne, M.S.; Anton, D.L.; DiCosimo, R. Glyoxylic Acid Production Using Microbial Transformant Catalysts. J. Org. Chem., 1995, 60, 3957-3963.
18. Horváth, I.T. Facile catalyst separation without water: fluorous biphase hydroformylation of olefins. Science, 1994, 266, 72-75.
19. Gladysz, J. A.; Emnet, C. In: Handbook of Fluorous Chemistry; Gladysz, Curran, Horváth, Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2005; pp. 11-23.
20. Carreira, M.; Contel, M. In: Fluorous Chemistry; Horváth, Ed.; Springer Berlin: Berlin, Heidelberg, 2012; Vol. 308, pp. 247-274.
21. Yi, W.-B.; Cai, C.; Wang, X. A novel ytterbium/perfluoroalkylated-pyridine catalyst for Baylis-Hillman reactions in a fluorous biphasic system. J. Fluorine Chem., 2007, 128, 919-924.
22. Yi, W.-B.; Cai, C.; Wang, X. Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth(III) perfluorooctanesulfonate catalysts in fluorous media. J. Fluorine Chem., 2006, 127, 1515-1521.
23. Dobbs, A. P.; Kimberley, M. R. Fluorous phase chemistry: a new industrial technology. J. Fluorine Chem., 2002, 118, 3-17.
24. Heydari, A.; Khaksar, S.; Tajbakhsh, M. Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates. Tetrahedron Lett., 2009, 50, 77-80.
25. Aghmiz, A.; Claver, C.; Masdeu-Bultó, A.M.; Maillard, D.; Sinou, D. Hydroformylation of 1-octene with rhodium catalysts in fluorous systems. J. Mol. Catal. A: Chem., 2004, 208, 97-101.
26. Caballero, A.; Perez, P. J.; Fuentes, M. A.; Etienne, M.; Munoz, B. K.; Abstracts of Papers, 244th ACS National Meeting & Exposition: Philadelphia, PA, United States, August 19-23, 2012, pp. INOR-464
27. Haviv, F.; Ratajczyk, J.D.; DeNet, R.W.; Kerdesky, F.A.; Walters, R.L.; Schmidt, S.P.; Holms, J.H.; Young, P.R.; Carter, G.W. 3-[I-(2-Benzoxazolyl) hydrazinolpropanenitrile Derivatives: Inhibitors of Immune Complex Induced Inflammation. J. Med. Chem., 1988, 31, 1719-1728.
28. Tsuji, K.; Ishikawa, H. Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7. Bioorg. Med. Chem. Lett., 1994, 4, 1601-1606.
29. Bell, F.W.; Cantrell, A.S.; Hoegberg, M.; Jaskunas, S.R.; Johansson, N.G.; Jordon, C.L.; Kinnick, M.D.; Lind, P.; Morin, J.M.; Noreen, R.; Oberg, B.; Palkowitz, J.A.; Parrish, C.A.; Pranc, P.; Sahlberg, C.; Ternansky, R.J.; Vasileff, R.T.; Vrang, L.; West, S.J.; Zhang, H.; Zhou, X.-X. Phenethylthiazolethiourea (PEW) Compounds, a New Class of HIV-1 Reverse Transcriptase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies of PEW Analogs. J. Med. Chem., 1995, 38, 4929-4936.
30. Zang, H.; Wang. M.; Cheng, B.W.; Song, J. Ultrasound-promoted synthesis of oximes catalyzed by a basic ionic liquid [bmIm]OH. Ultrasonics Sonochem., 2009, 16, 301-303.
31. Yannai, X.; Ge, S.; Rennert, G.; Gruener, N.; Fares, F.A. 3,3'-Diindolylmethane induces apoptosis in human cancer cells. Biochem. Biophys. Res. Comm., 1996, 228, 153-158.
32. Yuan, X.H.; Chen, M.; Dai, Q.X.; Cheng, X.N. Friedel-Crafts acylation of anthracene with oxalyl chloride catalyzed by ionic liquid of [bmim]Cl/AlCl3. Chem. Eng. J., 2009, 146, 266-269.
33. Bonacorso, H.G.; Wentz, A.P.; Lourega, R.V.; Cechinel, C.A.; Moraes, T.S.; Coelho, H.S.; Zanatta, N.; Martins, M.A.P.; Hörner, M.; Alves, S.H. Trifluoromethyl-containing pyrazolinyl (p-tolyl) sulfones: The synthesis and structure of promising antimicrobial agents. J. Fluorine. Chem., 2006, 127, 1066-1072.
34. Gong, K.; Fang, D.; Wang, H.-L.; Zhou, X.-L.; Liu, Z.-L. The one-pot synthesis of 14-alkyl-or aryl-14H-dibenzo[a, j]xanthenes catalyzed by taskspecific ionic liquid. Dyes Pigments, 2009, 80, 30-33.
35. Jadidi, K.; Ghahremanzadeh, R.; Asgari, D.; Eslami, P.; Arvin-Nezhad, H. Eco-friendly synthesis of 1,4-benzodiazepine-2,5-diones in the ionic liquid [bmim]Br. Monatsh. Chem., 2008, 139, 1229-1232.
36. Moreira, D.N.; Frizzo, C.P.; Longhi, K.; Zanatta, N.; Bonacorso, H.G.; Martins, M.A.P. An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5-dihydro-1H-pyrazoles in ionic liquid. Monatsh. Chem., 2008, 139, 1049-1054.
37. Wakamatsu, H.; Saito, Y.; Masabuchi, M.; Fujita, R. Synthesis of Imidazolium-Tagged Ruthenium Carbene Complex: Remarkable Activity and Reusability in Regard to Olefin Metathesis in Ionic Liquids. Synlett, 2008, 12, 1805-1808.
38. Suresh; Sandhu, J.S. Knoevenagel reaction: alum-mediated efficient green condensation of active methylene compounds with arylaldehydes. Green Chem. Lett. Rev., 2009, 2, 189-192.
39. Zhang, Y.; Xia, C. Magnetic hydroxyapatite-encapsulated α-Fe2O3 nanoparticles functionalized with basic ionic liquids for aqueous Knoevenagel condensation. Appl. Cata. A: Gen., 2009, 366, 141-147.
40. Wang, W.-J.; Cheng, W.-P.; Shao, L.-L.; Liu, C.-H.; Yang, J.-G. Henry and Knoevenagel reactions catalyzed by methoxyl propylamine acetate ionic liquid. Kinet. Cata., 2009, 50, 186-191.
41. Carrignon, C.; Makowski, P.; Antonietti, M.; Goettmann, F. Chloride ion pairs as catalysts for the alkylation of aldehydes and ketones with C-H acidic compounds. Tetrahedron Lett., 2009, 50, 4833-4837.
42. Yadav, L.D.S.; Singha, S.; Rai, V.K. A one-pot [Bmim]OH-mediated synthesis of 3-benzamidocoumarins. Tetrahedron Lett., 2009, 50, 2208-2212.
43. Zhou, Z.; Yuan, J.; Yang, R. Efficient Knoevenagel condensation catalyzed by 2-hydroxyethylammonium acetate under solvent-free conditions at room temperature Synth. Commun., 2009, 39, 2001-2007.
44. Suresh; Kumar, D.; Sandhu, J.S. An efficient green protocol for the production of 1,8-dioxo-octahydroxanthenes in triethylammonium acetate (TEAA), a recyclable inexpensive ionic liquid. J. Chem., 2009, 2, 937-940.
45. Suresh; Kumar, D.; Sandhu, J.S. Bismuth(III) chloride-mediated, efficient, solvent-free, MWI-enhanced Doebner condensation for the synthesis of (E)-cinnamic acids. Synth. Commun., 2010, 40, 1915-1919.
46. Jiang, D.; Wang, Y.Y.; Xu, Y.N.; Dai, L.Y. Doebner condensation in ionic liquids [Bmim]BF4 and [Bpy]BF4 to synthesize α, β-unsaturated carboxylic acid. Chin. Chem. Lett., 2009, 20, 279-282.
47. Ni, B.; Zhang, Q.; Dhungana, K.; Headley, A.D. Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide, a Recyclable Organocatalyst for the highly enantioselective Michael Addition to Nitroolefins. Org. Lett., 2009, 11, 1037-1040.
48. Singh, P.; Kumari, K.; Katyal, A.; Kalra, R.; Chandra, R. Copper Nanoparticles in Ionic Liquid: An Easy and Efficient Catalyst for Selective Carba-Michael Addition Reaction. Catal. Lett., 2009, 127, 119-125.
49. Kolosov, M.A.; Orlov, V.D.; Beloborodov, D.A.; Dotsenko, V.V. A chemical placebo. NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis. Mol. Divers., 2009, 13, 5-25.
50. Suresh, A.; Saini, A.; Kumar, D.; Sandhu, J. S. Multicomponent eco-friendly synthesis of 3,4-dihydropyrimidine-2-(1H)-ones using an organocatalyst Lactic acid. Green Chem. Lett. Rev., 2009, 2, 29-33.
51. Chavan, S.S.; Sharma, Y.O.; Degani, M.S. Cost-effective ionic liquid for environmentally friendly synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Green Chem. Lett. Rev., 2009, 2, 175-179.
52. Suresh; Kumar, D.; Sandhu, J.S. New efficient protocol for the production of Hantzsch 1,4-dihydropyridines using RuCl3. Synth. Commun., 2009, 39, 1957-1965.
53. Kumar, D.; Saini, A.; Suresh; Sandhu, J.S. Gallium(III) chloride as an efficient new catalyst for the production of Hantzsch 1,4-dihydropyridines. Indian Chem. Soc., 2009, 86, 996-1000.
54. Suresh; Sandhu, J.S. Recent advances in ionic liquids. Green unconventional solvents of this century. Part II. Green Chem. Lett. Rev., 2011, 4, 311-320.
55. Vollmer, C.; Thomann, R.; Janiak, C. Organic carbonates as stabilizing solvents for transition-metal nanoparticles. Dalton Trans., 2012, 41, 9722-9727.
56. Schäffner, B.; Verevkin, S. P.; Börner, A. Green solvents for synthesis and catalysis. Organic carbonates, Chem. Unserer Zeit, 2012, 43, 12-21.
57. Schäffner, B.; Holz, J.; Verevkin, S. P.; Börner A. Rhodium-catalyzed asymmetric hydrogenation with self-assembling catalysts in propylene carbonate. Tetrahedron Lett., 2008, 49(5), 768-771.
58. Schäffner, B.; Andrushko, V.; Bayardon, J.; Holz, J.; Börner, A. Organic carbonates as alternative solvents for asymmetric hydrogenation. Chirality, 2009, 21(9), 857-861.
59. Schäffner, B.; Holz, J.; Verevkin, S. P.; Börner A. Organic carbonates as alternative solvents for palladium-catalyzed substitution reactions. Chem-SusChem, 2008, 1(3), 249-253.
60. Leitner, W. Supercritical Carbon Dioxide as a Green Reaction Medium for Catalysis Acc. Chem. Res., 2002, 35, 746-756.
61. Ren, W.; Rutz, B.; Scurto, A. M. High-pressure phase equilibrium for the hydroformylation of 1-octene to nonanal in compressed CO2. J. of Supercritical Fluids, 2009, 51, 142-147.
62. Koeken, A. C. J.; van Vliet, M. C. A.; van den Broeke, L. J. P; Deelman, B. J.; Keurentjes, J. T. F. Selectivity of rhodium-catalyzed hydroformylation of 1-octene during batch and semi-batch reaction using trifluoromethylsubstituted ligands. Adv. Synth. Catal., 2008, 350, 179-188.
63. Frisch, A. C.; Webb, P. B.; Zhao, G.; Muldoon, M. J.; Pogorzelec, P. J.; Cole-Hamilton, D. J. Emerging Strategies in Catalysis. Dalton Trans., 2007, 5531-5538.
64. Li, C. J.; Trost, B. M. Green chemistry for chemical synthesis. PNAS, 2008, 105, 13197-13202.
65. Melo, C. I.; Bogel-Óukasik, R.; Gomes da Silva, M.; Bogel-Óukasik, E. Advantageous heterogeneously catalysed hydrogenation of carvone with supercritical carbon dioxide. Green Chem., 2011, 13, 2825-2830.
66. Endalkachew, S. D.; Venu, G. D.; Ashraf, A. H. Hydrogenation of Anthracene in Supercritical Carbon Dioxide Solvent Using Ni Supported on Hi-Zeolite Catalyst. Catalysts, 2012, 2, 85-100.
67. Chen, Y.; Wu, Y.; Zhang, Y.; Long, L.; Tao, L.; Yang, M.; Tang, M. Journal of Molecular Catalysis A: Chemical, 2012, 352, 102-109.
68. Bandres, M.; de Caro, P.; Thiebaud-Roux, S.; Borredon, M.-E. C. R. Green syntheses of biobased solvents. Chimie, 2011, 14(7-8), 636-646.
69. Gu, Y. Multicomponent reactions in unconventional solvents: state of the art. Green Chem., 2012, 14, 2091-2128.
70. Li, M.; Chen, C.; He, F.; Gu, Y. Multicomponent Reactions of 1,3-Cyclohexanediones and Formaldehyde in Glycerol: Stabilization of Paraformaldehyde in Glycerol Resulted from using Dimedone as Substrate. Adv. Synth Catal., 2010, 352(2+3), 519-530.
71. Tan, J.-N.; Li, M.; Gu, Y. Multicomponent reactions of 1,3-disubstituted 5-pyrazolones and formaldehyde in environmentally benign solvent systems and their variations with more fundamental substrates. Green Chem., 2010, 12, 908-914.
72. Quan, Z.-J.; Ren, R.-G.; Da, Y.-X.; Zhang, Z.; Wang, X.-C. Glycerol as an Alternative Green Reaction Medium for Multicomponent Reactions Using PS-PEG-OSO3H as Catalyst. Synth. Comm., 2011, 41, 3106-3116.