Application of bio-based solvents in catalysis

Current Organic Synthesis

Volumn 12, Issue 6, 2015, Pages 675-695

  Corrêa, Arlene G ^a   Paixão, Márcio W ^a   Schwab, Ricardo S ^a  

^a FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

Author keywords

Biocatalysis; Green chemistry; Metal based catalysis; Organocatalysis; Renewable solvents

Indexed keywords

EID: 84942099402     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017941206150828102108     Document Type: Article

References (108)

1. Anastas, P.T.; Williamson, T.C. In: Green Chemistry. Designing Chemistry for the Environment; Eds.; Anastas, P.T.; Williamson, T.C.; ACS Symposium Series, 1996, Ch. 1; Vol. 626, pp. 1-17.
2. R. A. Sheldon, Organic synthesis; past, present and future, Chem. Ind. 1992, 903-906
3. Sheldon. R.A. Fundamentals of green chemistry: efficiency in reaction design. Chem. Soc. Rev. 2012, 41, 1437-1451.
4. Moity, L. Benazzouz, A.; Molinier, V.; Nardello-Rataj, V.; Elmkaddem, M.K.; de Caro, P.; Thiébaud-Roux, Gerbaud, V.; Marion, P.; Aubry, J.-M. Glycerol acetals and ketals as bio-based solvents: positioning in Hansen and Cosmo-RS spaces, volatility and stability towards hydrolysis and autoxidation. Green Chem. 2015, 17, 1779-1792.
5. Isley, N.A.; Hageman, M.S.; Lipshultz, B.H. Dehalogenation of functionalized alkyl halides in water at room temperature. Green Chem. 2015, 17, 893-897.
6. Kerton, F. M. Alternative Solvents for Green Chemistry, RSC Publ., Cambridge, UK, 2009.
7. Bryan, M.C.; Dillon, B.; Hamann, L.G.; Hughes, G.J.; Kopach, M.E.; Peterson, E.A.; Pourashraf, M.; Raheem, I.; Richardson, P.; Richter, D.; Sneddon, H. F. Sustainable Practices in Medicinal Chemistry: Current State and Future Directions. J. Med. Chem. 2013, 56, 6007-6021.
8. Alfonsi, K.; Colberg, J.; Dunn, P.J.; Fevig, T.; Jennings, S.; Johnson,T.A.; Kleine, H.P.; Knight, C.; Nagy, M.A.; Perry, D.A.; Stefaniak, M. Green chemistry tools to influence a medicinal chemistry and research chemistry based organization. Green Chem. 2008, 10, 31-36.
9. Henderson, R.K.; Jimenez-Gonzalez, C.; Constable, D.J.C.; Alston, S.R.; Inglis, G.G.A.; Fisher, G.; Sherwood, J.; Binks, S.P.; Curzons, A.D. Expanding GSK's solvent selection guide-embedding sustainability into solvent selection starting at medicinal chemistry. Green Chem. 2011, 13, 854-862.
10. Prat, D.; Pardigon, O.; Flemming, H.-W.; Letestu, S.; Ducandas, V.; Isnard, P.; Guntrum, E.; Senac, T.; Ruisseau, S.; Cruciani, P.; Hosek, P. Sanofi's Solvent Selection Guide: A Step Toward More Sustainable Processes. Org. Process Res. Dev. 2013, 17, 1517-1525.
11. Capello, C.; Fischer, U.; Hungerbühler, K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem. 2007, 9, 927-934.
12. Leitner, W.; Jessop, P.G. In: Handbook of Green Chemistry: Green Solvents-Supercritical Solvents; Ed.; Anastas, P. T., Wiley-VCH, Weinheim, 2013; Vol. 4, pp. 1-508.
13. Qureshi, Z.S.; Deshmukh, K.M.; Bhanage, B.M. Applications of ionic liquids in organic synthesis and catalysis. Clean Technol. Environ. Pol. 2014, 16, 1487-1513.
14. Pham, T. P.T.; Cho, C.W.; Yun, Y.S. Environmental fate and toxicity of ionic liquids: A review. Water Res. 2010, 44, 352-372.
15. Gu, Y.; Jérôme, F. Bio-Based Solvents: an Emerging Generation of Fluids for the Design of Eco-Efficient Processes in Catalysis and Organic Chemistry. Chem. Soc. Rev. 2013, 42, 9550-9570.
16. Bandres, M.; de Caro, P.; Borredon M.-E. Green syntheses of biobased solvents, C. R. Chimie, 2011, 14, 636-646.
17. Kerton, F M.; Marriott, R. Alternative Solvents for Green Chemistry, 2nd ed.; RSC Green Chemistry Series: Cambridge, 2013.
18. Pace, V.; Hoyos, P.; Castoldi, L.; de María, P.D.; Alcántara, A. R. A 2-Methyltetrahydrofuran (2-MeTHF): Biomass-Derived Solvent with Broad Application in Organic Chemistry. ChemSusChem. 2012, 5, 1369-1379.
19. Aycock, D. F. Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions Org. Process Res. Dev. 2007, 11, 156-159.
20. Pereira, C. S.M.; Silva, V.M.T.M.; Rodrigues, A. E. Ethyl lactate as a solvent: Properties, applications and production processes -a review. Green Chem. 2011, 13, 2658-2671.
21. Aparicio, S.; Alcalde, R. The green solventethyl lactate: an experimental and theoretical characterization. Green Chem. 2009, 11, 65-78.
22. Zhou, C.-H.; Beltramini, J.N.; Fan, Y.-X.; Lu, C. Q. Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem. Soc. Rev. 2008, 37, 527-549.
23. Sonnati, M.O.; Amigoni, S.; Givenchy, E. P.T.; Darmanin, T.; Choulet, O.; Guittard. F. Glycerol carbonate as a versatile building block for tomorrow: synthesis, reactivity, properties and applications. Green Chem., 2013, 15, 283-306.
24. Pagliaro, M.; Ciriminna, R.; Kimura, H.; Rossi, M.; Della Pina, C. From glycerol to value-added products. Angew. Chem. Int. Ed. 2007, 46, 4434-4040.
25. Díaz-Álvarez, A.; Francos, J.; Crochet, P.; Cadierno, V. Recent Advances in the Use of Glycerol as Green Solvent for Synthetic Organic Chemistry. Curr. Green Chem. 2014, 1, 51-65.
26. García, J.I.; García-Marín, H.; Pires E. Glycerol Based Solvents: Synthesis, Properties and Applications. Green Chem. 2014, 16, 1007-1033.
27. Cintas, P.; Tagliapietra, S.; Calcio Gaudino, E.; Palmisano, G.; Cravotto, G. Glycerol: A Solvent and a Building Block of Choice for Microwave and Ultrasound Irradiation Procedures. Green Chem. 2014, 16, 1056-1065.
28. Diaz-Alvarez, A.E.; Francos, J.; Lastra-Barreira, B.; Crochet, P.; Cadierno, V. Glycerol and Derived Solvents: New Sustainable Reaction Media for Organic Synthesis. Chem. Commun. 2011, 47, 6208-6227.
29. Ou, G.; He, B.; Li, X.; Lei, J. Glycerol Carbonate: A Novel Biosolvent with Strong Ionizing and Dissociating Powers. Sci. World J. 2012, 697161.
30. Chahdoura, F.; Favier, I.; Gómez, M. Glycerol as Suitable Solvent for the Synthesis of Metallic Species and Catalysis. Chem. Eur. J. 2014, 20, 10884-10893.
31. Zhang, Q.; Vigier, K.O.; Royer, S.; Jérôme, F. Deep eutectic solvents: syntheses, properties and applications. Chem. Soc. Rev. 2012, 41, 7108-7146.
32. Smith, E.L.; Abbott, A.P.; Ryder, K. S. Deep Eutectic Solvents (DESs) and Their Applications. Chem. Rev. 2014, 114, 11060-11082.
33. γ-Valerolactone as a Renewable Dipolar Aprotic Solvent Deriving from Biomass Degradation for the Hiyama Reaction. Ismalaj, E.; Strappaveccia, G.; Ballerini, E.; Elisei, F.; Piermatti, O.; Gelman, D.; Vaccaro, L. ACS Sustainable Chem. Eng. 2014, 2, 2461-2464.
34. Alonso, D.M.; Wettstein, S.G.; Dumesic, J.A. Gamma-valerolactone, a sustainable platform molecule derived from lignocellulosic biomass. Green Chem. 2013, 15, 584-595.
35. Ciriminna, R.; Lomeli-Rodriguez, M.; Cara, P.D.; Lopez-Sanchez, J.A.; Pagliaro, M. Limonene: a versatile chemical of the bioeconomy. Chem. Commun. 2014, 50, 15288-15296.
36. Clark, J.H.; Macquarrie, D.J.; Sherwood, J. A quantitative comparison between conventional and bio-derived solvents from citrus waste in esterification and amidation kinetic studies. Green Chem. 2012, 14, 90-93.
37. Sherwood, J.; De Bruyn, M.;Constantinou, A.; Moity, L.; McElroy, C.R.; Farmer, T.J.; Duncan, T.; Raverty, W.; Hunt, A.J.; Clark, J.H. Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents. Chem. Commun. 2014, 50, 9650-9652.
38. Díaz-Álvarez, A.E.; Cadierno, V. Glycerol: A promising Green Solvent and Reducing Agent for Metal-Catalyzed Transfer Hydrogenation Reactions and Nanoparticles Formation. Appl. Sci. 2013, 3, 55-69.
39. Tarama, K.; Funabiki, T. Butadiene Hydrogenation by Pentacyanocobaltate (II) in Glycerin Solvent. Bull. Chem. Soc. Jpn. 1968, 41, 1744.
40. Funabiki, T.; Tarama, K. The Hydrogenation of Butadiene Catalyzed by Pentacyanocobaltate (II) in Aqueous and Non-aqueous Solvents. Bull. Chem. Soc. Jpn. 1971, 44, 945-951.
41. Wolfson, A.; Dlugy, C. Palladium-Catalyzed Heck and Suzuki Coupling in Glycerol. Chem. Papers 2007, 61, 228-232.
42. Wolfson, A.; Litvak, G.; Dlugy, C.; Shotland, Y.; Tavor, D. Employing crude glycerol from biodiesel production as an alternative green reaction medium. Ind. Crops Prod. 2009, 30, 78-81.
43. Baig, R. B.N.; Varma, R. S. Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis. Chem. Soc. Rev. 2012, 41, 1559-1584.
44. Cravotto, G.; Orio, L.; Gaudino, E.C.; Martina, K.; Tavor, D.; Wolfson, A. Efficient synthetic protocols in glycerol under heterogeneous catalysis. ChemSusChem 2011, 4, 1130-1134.
45. Azua, A.; Mata, J.A.; Heymes, P.; Peris, E.; Lamaty, F.; Martinez, J.; Colacino E. Palladium N-Heterocyclic Carbene Catalysts for Ultrasound-Promoted Suzuki-Miyaura Reaction in Glycerol. Adv. Synth. Catal. 2013, 355, 1107-1116.
46. Grace, A.N.; Pandian, K. One pot synthesis of polymer protected Pt, Pd, Ag and Ru nanoparticles and nanoprisms under reflux and microwave mode of heating in glycerol-A comparative study. Mater. Chem. Phys. 2007, 104, 191-198.
47. Adrio, L.A.; Nguyen, B.N.; Guilera, G.; Livingston, A.G.; Hii, K. K. Speciation of Pd(OAc)2 in ligandless Suzuki-Miyaura reactions. Catal. Sci. Technol. 2012, 2, 316-325.
48. Banik, B.; Tairai, A.; Shahnaz, N.; Das, P. Palladium(II) complex with a potential N4-type Schiff-base ligand as highly efficient catalyst for Suzuki-Miyaura reactions in aqueous media. Tetrahedron Lett. 2012, 53, 5627-5630.
49. Cintas, P.; Cravotto, G.; Gaudino, E.C.; Orio, L.; Boffa, L. Reticulated Pd(ii)/Cu(i) cyclodextrin complexes as recyclable green catalyst for Sonogashira alkynylation. Catal. Sci. Technol. 2012, 2, 85-87.
50. Gonçalves, L.C.; Fiss, G.F.; Perin, G.; Alves, D.; Jacob, R.G.; Lenardão, E. J. Glycerol as a promoting medium for cross-coupling reactions of diaryl diselenides with vinyl bromides. Tetrahedron Lett. 2010, 51, 6772-6775.
51. Ricordi, V.G.; Freitas, C.S.; Perin, G.; Lenardão, E.J.; Jacob, R.G.; Savegnago, L.; Alves, D. Glycerol as a recyclable solvent for coppercatalyzed cross-coupling reactions of diaryl diselenides with aryl boronic acids. Green Chem. 2012, 14, 1030-1034.
52. Khatri, P.K.; Jain, S. L. Glycerol ingrained copper: an efficient recyclable catalyst for the N-arylation of amines with aryl halides. Tetrahedron Lett. 2013, 54, 2740-2743.
53. Yadav, D. K.T.; Rajak, S.S.; Bhanage, B. M. N-arylation of indoles with aryl halides using copper/glycerol as a mild and highly efficient recyclable catalytic system. Tetrahedron Lett. 2014, 55, 931-935.
54. Chahdoura, F.; Pradel, C.; Gómez, M. Copper (I) Oxide Nanoparticles in Glycerol: A Convenient Catalyst for Cross-Coupling and Azide-Alkyne Cycloaddition Processes. ChemCatChem 2014, 6, 2929-2936.
55. Chahdoura, F.; Pradel, C.; Gómez, M. Palladium Nanoparticles in Glycerol: A Versatile Catalytic System for C-X Bond Formation and Hydrogenation Processes. Adv. Synth. Catal. 2013, 355, 3648-3660.
56. Vidal, C.; García-Álvarez, J. Glycerol: a biorenewable solvent for base-free Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes. Highly efficient transformations and catalyst recycling. Green Chem. 2014, 16, 3515-3521.
57. Delample, M.; Villandier, N.; Douliez, J.P.; Camy, S.; Condoret, J.S.; Pouilloux, Y.; Barrault, J.; Jerome, F. Glycerol as a cheap, safe and sustainable solvent for the catalytic and regioselective β,β-diarylation of acrylates over palladium nanoparticles. Green Chem. 2010, 12, 804-808.
58. Wan, J.-P.; Liu, Y. Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines. RSC Adv. 2012, 2, 9763-9777.
59. Narsaiah, A.V.; Nagaiah, B. Glycerine-CeCl3·7H2O: An Efficient Recyclable Reaction Medium for the Synthesis of Hantzsch Pyridines. Asian J. Chem. 2010, 22, 8099-8106.
60. Narsaiah, A.V.; Kumar, J. K. Glycerin and CeCl3·7H2O: A New and Efficient Recyclable Reaction Medium for the Synthesis of Quinoxalines. Synth. Commun. 2012, 42, 883-892.
61. Carmona, R.C.; Schevciw, E.P.; de Albuquerque, J. L.P.; Wendler, E.P.; Dos Santos, A. A. Joint use of microwave and glycerol-zinc (II) acetate catalytic system in the synthesis of 2-pyridyl-2-oxazolines. Green Proc. Synth. 2013, 2, 35-42.
62. Silveira, C.C.; Mendes, S.R.; Líbero, F.M.; Lenardão, E.J.; Perin, G. Glycerin and CeCl3·7H2O: a new and efficient recyclable medium for the synthesis of bis(indolyl)methanes. Tetrahedron Lett. 2009, 50, 6060-6063.
63. Narsaiah, A.; Wadavrao, S.; Reddy, A.; Yadav, J. Glycerine and CeCl3.7H2O: An Efficient and Recyclable Reaction Medium for Ring Opening of Epoxides with Thioamides and Amines. Synthesis 2011, 485-489.
64. Francos, J.; Cadierno, V. Palladium-catalyzed cycloisomerization of (Z)-enynols into furans using green solvents: glycerol vs. water. Green Chem. 2010, 12, 1552-155.
65. Chahdoura, F.; Dubrulle, L.; Fourmy, K.; Durand, J.; Madec, D.; Gómez, M. Glycerol -A Non-Innocent Solvent for Rh-Catalysed Pauson-Khand Carbocyclisations. Eur. J. Inorg. Chem. 2013, 2013, 5138-5144.
66. Tomasek, J.; Schatz J. Olefin metathesis in aqueous media. Green Chem. 2013, 15, 2317-2338.
67. Vougioukalakis, G.C.; Grubbs, R.H. Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts. Chem. Rev. 2010, 110, 1746-1787.
68. Burtscher, D.; Grela, K. Aqueous Olefin Metathesis. Angew. Chem. Int. Ed. 2009, 48, 442-454.
69. Bakhrou, N.; Lamaty, F.; Martinez, J.; Colacino, E. Ring-closing metathesis in glycerol under microwave activation. Tetrahedron Lett. 2010, 51, 3935-3937.
70. Seyedi, N. Glycerin and [Iron(III)(salen)]Cl as an efficient catalytic medium for multicomponent reactions. Transition Met. Chem. 2013, 38, 93-103.
71. García, J.I.; García-Marín, H.; Mayoral, J.A.; Pérez, P. Green solvents from glycerol. Synthesis and physico-chemical properties of alkyl glycerol ethers. Green Chem. 2010, 12, 426-434.
72. Aldea, L.; Fraile, J.M.; García-Marín, H.; García, J.I.; Herrerías, C.I.; Mayoral, J.A.; Pérez, I. Study of the recycling possibilities for azabis(oxazoline)-cobalt complexes as catalysts for enantioselective conjugate reduction. Green Chem. 2010, 12, 435-440.
73. Aldea, L.; Garcia, J.I.; Mayoral, J. A. Multiphase enantioselective Kharasch-Sosnovsky allylic oxidation based on neoteric solvents and copper complexes of ditopic ligands. Dalton Trans. 2012, 41, 8285-8289.
74. Sutter, M.; Pehlivan, L.; Lafon, R.; Dayoub, W.; Raoul, Y.; Métay, E.; Lemaire, M. 1,2,3-Trimethoxypropane, a glycerol-based solvent with low toxicity: new utilization for the reduction of nitrile, nitro, ester, and acid functional groups with TMDS and a metal catalyst. Green Chem. 2013, 15, 3020-3026.
75. Behr, A.; Bahke, P.; Klinger, B.; Becker, M. Application of carbonate solvents in the telomerisation of butadiene with carbon dioxide. J. Mol. Catal. A: Chem. 2007, 267, 149-156.
76. Wolfson, A.; Snezhko, A.; Meyouhas, T.; Tavor, D. Glycerol derivatives as green reaction mediums. Green Chem. Lett. Rev. 2012, 5, 7-12.
77. Wolfson, A.; Dlugy, C.; Mordechaiev, I.; Sliman, T.; Tavor, D. Glycerol triacetate mixtures as green reaction mediums. Can. J. Chem. 2014, 92, 240-242.
78. Strappaveccia, G.; Luciani, L.; Bartollini, E.; Marrocchi, A.; Pizzo, F.; Vaccaro, L. γ-Valerolactone as an alternative biomass-derived medium for the Sonogashira reaction. Green Chem. 2015, 17, 1071-1076.
79. Ismalaj, E.; Strappaveccia, G.; Ballerini, E.; Elisei, F.; Piermatti, O.; Gelman, D.; Vaccaro, L. γ-Valerolactone as a Renewable Dipolar Aprotic Solvent Deriving from Biomass Degradation for the Hiyama Reaction. ACS Sustainable Chem. Eng. 2014, 2, 2461-2464.
80. Strappaveccia, G.; Ismalaj, E.; Petrucci, C.; Lanari, D.; Marrocchi, A.; Drees, M.; Facchetti, A.; Vaccaro, L. A biomass-derived safe medium to replace toxic dipolar solvents and access cleaner Heck coupling reactions. Green Chem. 2015, 17, 365-372.
81. Krause, N.; Hoffmann-Röder, A. Recent Advances in Catalytic Enantioselective Michael Additions. Synthesis 2001, 171-196.
82. Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Recent Advances in Metal-Catalyzed Asymmetric Conjugate Additions. Synthesis, 2007, 1279-1300.
83. Robert, T.; Velder, J.; Schmalz, H. G. Enantioselective Cu-catalyzed 1,4-addition of Grignard reagents to cyclohexenone using taddol-derived phosphine-phosphite ligands and 2-methyl-THF as a solvent. Angew. Chem. Int. Ed. 2008, 47, 7718-7721.
84. Naeemi, Q.; Robert, T.; Kranz, D.P.; Velder, J.; Schmalz, H.-G. Chiral phosphine-phosphite ligands in the enantioselective 1,4-addition of Grignard reagents to α,β-unsaturated carbonyl compounds. Tetrahedron: Asymmetry 2011, 22, 887-892.
85. Milton, E.J.; Clarke, M. L. Palladium-catalysed Grignard cross-coupling using highly concentrated Grignards in methyl-tetrahydrofuran. Green Chem. 2010, 12, 381-383.
86. Ramgren, S.D.; Hie, L.; Ye, Y.; Garg, N.K. Nickel-Catalyzed Suzuki Miyaura Couplings in Green Solvents. Org. Lett. 2013, 15, 3950-3953
87. Fine Nathel, N.F.; Kim, J.; Hie, L.; Jiang, X.; Garg, N. K. Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF. ACS catalysis 2014, 4, 3289-3293.
88. Koenig, S.G.; Dankwardt, J.W.; Liu, Y.; Zhao, H.; Singh, S. P. Copper-Catalyzed Synthesis of Indoles and Related Heterocycles in Renewable Solvents. ACS Sustainable Chem. Eng. 2014, 2, 1359-1363.
89. Smoleń, M.; Kędziorek, M.; Grela, K. 2-Methyltetrahydrofuran: Sustainable solvent for ruthenium-catalyzed olefin metathesis. Catal. Commun. 2014, 44, 80-84.
90. Monks, B.M.; Fruchey, E.R.; Cook, S. P. Iron-catalyzed C(sp(2))-H alkylation of carboxamides with primary electrophiles. Angew. Chem. Int. Ed. 2014, 53, 11065-11069.
91. Wan, J.-P.; Wang, C.; Zhou, R.; Liu, Y. Sustainable H2O/ethyl lactate system for ligand-free Suzuki-Miyaura reaction. RSC Adv. 2012, 2, 8789-8792.
92. Wan, J.-P.; Cao, S.; Jing, Y. Copper-catalyzed homo-and cross-coupling reactions of terminal alkynes in ethyl lactate. Appl. Organomet. Chem. 2014, 28, 631-634.
93. Edwards, G.A.; Trafford, M.A.; Hamilton, A.E.; Buxton, A.M.; Bardeaux, M.C.; Chalker, J. M. Melamine and melamine-formaldehyde polymers as ligands for palladium and application to Suzuki-Miyaura cross-coupling reactions in sustainable solvents. J. Org. Chem. 2014, 79, 2094-2104.
94. Clark, J.H.; Macquarrie, D.J.; Sherwood, J. The Combined Role of Catalysis and Solvent Effects on the Biginelli Reaction: Improving Efficiency and Sustainability. Chem. Eur. J. 2013, 19, 5174-5182.
95. Bertelsen, S. Jørgensen, K. A. Organocatalysis-after the gold rush. Chem. Soc. Rev. 2009, 38, 2178-2189.
96. Giacalone, F.; Gruttadauria, M.; Agrigento, P.; Noto, R. Low-loading asymmetric organocatalysis. Chem. Soc. Rev. 2012, 41, 2406-2447.
97. García-Marín, H.; Van der Toorn, J.C.; Mayoral, J.A.; García, J.I.; Arends, I. W. C. E Glycerol-based solvents as green reaction media in epoxidations with hydrogen peroxide catalysed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide. Green Chem. 2009, 11, 1605-1609.
98. Muller, C.R.; Meiners, I.; Domínguez de María, P. Highly enantioselective tandem enzyme-organocatalyst crossed aldol reactions with acetaldehyde in deep-eutectic-solvents. RSC. Adv. 2014, 4, 46097-46101.
99. Yang, H.; Mahapatra, S.; Cheong, P. H-Y.; Carter, R. G. Highly Stereoselective and Scalable anti-Aldol Reactions Using N-(p-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: Scope and Origins of Stereoselectivities. J. Org. Chem. 2010, 75, 7279-7290.
100. Shanmuganathan, S.; Greiner, L.; Domínguez de María, P. Silicaimmobilized piperazine: A sustainable organocatalyst for aldol and Knoevenagel reactions. Tetrahedron Lett. 2010, 51, 6670-6672.
101. Pérez-Sánchez, M.; Domínguez de María, P. Synthesis of natural fragrance jasminaldehyde using silica-immobilized piperazine as organocatalyst. Catal. Sci. Technol., 2013, 3, 2732-2736.
102. Bellomo, A.; Daniellou, R.; Plusquellec, D. Aqueous solutions of facial amphiphilic carbohydrates as sustainable media for organocatalyzed direct aldol reactions. Green Chem. 2012, 14, 281-284.
103. Tao, J.; Liu, J.; Chen., Z. Some Recent Examples in Developing Biocatalytic Pharmaceutical Processes. In: Asymmetric Catalysis on Industrial Scale: Challenges, Approaches, and Solutions. H.U. Blaser and H. J. Federsel, Ed., 2nd ed., Wiley-VCH: Weinheim, 2010, pp. 3-12.
104. Paggiola, G. Biocatalysis in biosolvents. Chemist. Rev. 2014, 23, 24-28.
105. Perez-Sanchez, M.;Sandoval, M.; Hernaiz, M.; de Maria, Dominguez, P. Biocatalysis in Biomass-derived Solvents: The Quest for Fully Sustainable Chemical Processes. Curr. Org. Chem. 2013, 17, 1188-1199.
106. Paggiola, G.; Hunt, A.J.; McElroy, C.R.; Sherwood, J.; Clark, J. H. Biocatalysis in bio-derived solvents: an improved approach for medium optimization. Green Chem. 2014, 16, 2107-2110.
107. Bi, Y.H.; Duan, Z.Q.; Du, W.Y.; Wang, Z. Y. Improved synthesis of phosphatidylserine using bio-based solvents, limonene and p-cymene. Biotechnol. Lett. 2015, 37, 115-119.
108. Sandoval, M.; Hoyos, P.; Cortes, A.; Bavaro, T.; Terreni, M.; Hernaiz, M. J. Development of regioselective deacylation of peracetylated beta-Dmonosaccharides using lipase from Pseudomonas stutzeri under sustainable conditions that the area is largely unexplored, with plenty of exciting opportunities, 2014, 4, 55495-55502.