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Ionic liquids as substrate-specific recoverable solvents and catalysts of regio-, stereo- and enantioselective organic reactions

Sergei Grigorievich Zlotin 1
Sergei Grigorievich Zlotin
Nina Nikolaevna Makhova 1
Nina Nikolaevna Makhova
Published 2010-03-05
Focus articleVolume 20, Issue 2, 63-71
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Zlotin S. G., Makhova N. N. Ionic liquids as substrate-specific recoverable solvents and catalysts of regio-, stereo- and enantioselective organic reactions // Mendeleev Communications. 2010. Vol. 20. No. 2. pp. 63-71.
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Zlotin S. G., Makhova N. N. Ionic liquids as substrate-specific recoverable solvents and catalysts of regio-, stereo- and enantioselective organic reactions // Mendeleev Communications. 2010. Vol. 20. No. 2. pp. 63-71.
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TY - JOUR
DO - 10.1016/j.mencom.2010.03.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.03.001
TI - Ionic liquids as substrate-specific recoverable solvents and catalysts of regio-, stereo- and enantioselective organic reactions
T2 - Mendeleev Communications
AU - Zlotin, Sergei Grigorievich
AU - Makhova, Nina Nikolaevna
PY - 2010
DA - 2010/03/05
PB - Mendeleev Communications
SP - 63-71
IS - 2
VL - 20
ER -
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@article{2010_Zlotin,
author = {Sergei Grigorievich Zlotin and Nina Nikolaevna Makhova},
title = {Ionic liquids as substrate-specific recoverable solvents and catalysts of regio-, stereo- and enantioselective organic reactions},
journal = {Mendeleev Communications},
year = {2010},
volume = {20},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.03.001},
number = {2},
pages = {63--71},
doi = {10.1016/j.mencom.2010.03.001}
}
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Zlotin, Sergei Grigorievich, and Nina Nikolaevna Makhova. “Ionic liquids as substrate-specific recoverable solvents and catalysts of regio-, stereo- and enantioselective organic reactions.” Mendeleev Communications, vol. 20, no. 2, Mar. 2010, pp. 63-71. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.03.001.
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Abstract

The results obtained in the past few years concerning the use of ionic liquids and their congeners in reactions of organic compounds are summarized and the new opportunities opened by the use of such liquids instead of traditional organic solvents and catalysts are demonstrated.

References

1.
10.1016/j.mencom.2010.03.001_bib1
Pokhodenko
Teor. Eksp. Khim., 2002
2.
R. A. Sheldon, Chem. Ind. (London), 1992, 903.
3.
Atom efficiency and catalysis in organic synthesis
Sheldon R.A.
Pure and Applied Chemistry, 2000
4.
10.1016/j.mencom.2010.03.001_bib4
Kustov
Ross. Khim. Zh., 2004
5.
E factors, green chemistry and catalysis: an odyssey
Sheldon R.A.
Chemical Communications, 2008
7.
Applications of ionic liquids in the chemical industry
Plechkova N.V., Seddon K.R.
Chemical Society Reviews, 2008
8.
Thermal properties of imidazolium ionic liquids
Ngo H.L., LeCompte K., Hargens L., McEwen A.B.
Thermochimica Acta, 2000
10.
10.1016/j.mencom.2010.03.001_bib10
Freemantle
Science/Technology, 2000
11.
Ionic liquids. Green solvents for the future
Earle M.J., Seddon K.R.
Pure and Applied Chemistry, 2000
12.
N. V. Plechkova and K. R. Seddon, in Methods and Reagents for Green Chemistry, eds. P. Tundo, A. Perosa and F. Zecchini, John Wiley & Sons, Inc., Hoboken, New Jersey, 2007, pp. 105–130.
13.
A. Stark and K. R. Seddon, in Kirk–Othmer Encyclopedia of Chemical Technology, 5th edn., ed. A. Seidel, John Wiley & Sons, Inc., 2007, vol. 26, pp. 836–920.
14.
Design of Sustainable Chemical ProductsThe Example of Ionic Liquids
Ranke J., Stolte S., Störmann R., Arning J., Jastorff B.
Chemical Reviews, 2007
16.
Why ionic liquids can possess extra solvent power
Aerov A.A., Khokhlov A.R., Potemkin I.I.
Journal of Physical Chemistry B, 2006
17.
Using Kamlet−Taft Solvent Descriptors To Explain the Reactivity of Anionic Nucleophiles in Ionic Liquids
Crowhurst L., Falcone R., Lancaster N.L., Llopis-Mestre V., Welton T.
Journal of Organic Chemistry, 2006
18.
Brønsted Acids in Ionic Liquids: Fundamentals, Organic Reactions, and Comparisons
19.
Ionic Liquids in Synthesis, eds. P. Wasserscheid and T. Welton, Wiley- VCH Verlag GmbH & Co. KGaA, Weinheim, 2008, vol. 1.
20.
Ionic Liquids in Synthesis, eds. P. Wasserscheid and T. Welton, Wiley- VCH Verlag GmbH & Co. KGaA, Weinheim, 2008, vol. 2.
21.
Catalysis in Ionic Liquids
Pârvulescu V.I., Hardacre C.
Chemical Reviews, 2007
22.
Ionic liquids as a medium for enantioselective catalysis
Durand J., Teuma E., Gómez M.
Comptes Rendus Chimie, 2007
23.
Biocatalysis in Ionic Liquids
van Rantwijk F., Sheldon R.A.
Chemical Reviews, 2007
24.
Catalysts with ionic tag and their use in ionic liquids
Šebesta R., Kmentová I., Toma Š.
Green Chemistry, 2008
25.
E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Catalysis, 3rd edn., VCH Verlagsgesellschaft, Weinheim, 1993.
27.
Lewis base ionic liquids
MacFarlane D.R., Pringle J.M., Johansson K.M., Forsyth S.A., Forsyth M.
Chemical Communications, 2006
28.
One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Acidic Ionic Liquids Under Solvent-Free Conditions
30.
“Nonsolvent” Applications of Ionic Liquids in Biotransformations and Organocatalysis
Domínguez de María P.
Angewandte Chemie - International Edition, 2008
31.
S. G. Zlotin and N. N. Makhova, in Sintezy organicheskikh soedinenii, (Syntheses of Organic Compounds), ed. M. P. Egorov, Maks-Press, Moscow, 2008, vol. 3, p. 55.(in Russian).
32.
Kryshtal G.V., Zhdankina G.M., Zlotin S.G.
Mendeleev Communications, 2002
33.
Reactions of CH-acids with  , -unsaturated aldehydes in ionic liquids
Kryshtal G.V., Zhdankina G.M., Astakhova I.V., Zlotin S.G.
Russian Chemical Bulletin, 2004
34.
G. V. Krishtal, G. M. Zhdankina, A. A. Shestopalov, I. V. Astakhova, G. V. Evdokimova, N. A. Shinkova, S. S. Yufit and S. G. Zlotin, in Green Chemistry in Russia, eds. V. Lunin, P. Tundo and E. Lokteva, published by INCA in collaboration with IUPAC and INTAS, 2005, p. 29.
35.
L. S. Bondar and R. A. Okunev, Brit. Pat. GB 1,173,419.(Chem. Abstr., 1970, 72, 54770f).
36.
L. S. Bondar and R. A. Okunev, Ger. Offen. DE 1,801,868.(Chem. Abstr., 1970, 73, 34814r).
37.
L. S. Bondar, R. A. Okunev, L. V. Polezhaev, S. P. Kolchin, L. V. Cherkasova and L. F. Nikolaeva, US Pat. US 4,495,201.(Chem. Abstr., 1985, 102, 172652e).
40.
Alkyl 3,7,11-trimethyl-2,4-dodecadienoates, a new class of potent insect growth regulators with juvenile hormone activity
41.
E. P. Serebryakov and V. K. Promonenkov, in Itogi nauki i tekhniki. Organicheskaya khimiya (Advances in Science and Engineering. Organic Chemistry), VINITI, Moscow, 1989, vol. 9, p. 156.(in Russian).
43.
10.1016/j.mencom.2010.03.001_bib44
Shestopalov
Izv. Akad. Nauk, Ser. Khim., 2004
44.
Kucherenko A.S., Siyutkin D.E., Muraviev V.O., Struchkova M.I., Zlotin S.G.
Mendeleev Communications, 2007
45.
10.1016/j.mencom.2010.03.001_bib46
Kucherenko
Izv. Akad. Nauk, Ser. Khim., 2008
46.
10.1016/j.mencom.2010.03.001_bib47
Sheremetev
Mendeleev Commun., 2002
47.
Sheremetev A.B., Yudin I.L., Suponitsky K.Y.
Mendeleev Communications, 2006
48.
10.1016/j.mencom.2010.03.001_bib49
Shvekhgeimer
Usp. Khim., 1998
49.
Sheremetev A.B., Aleksandrova N.S., Dmitriev D.E.
Mendeleev Communications, 2006
50.
Nucleophilic routes to selectively fluorinated aromatics
Adams D.J., Clark J.H.
Chemical Society Reviews, 1999
51.
Zero-Hydrogen Furazan Macrocycles with Oxy and Azo Bridges
Sheremetev A.B., Kulagina V.O., Ivanova E.A.
Journal of Organic Chemistry, 1996
52.
Variation in the regioselectivity of levulinic acid bromination in ionic liquids
Zavozin A.G., Kravchenko N.E., Ignat’ev N.V., Zlotin S.G.
Tetrahedron Letters, 2010
53.
Seregin I.V., Batog L.V., Makhova N.N.
Mendeleev Communications, 2002
54.
10.1016/j.mencom.2010.03.001_bib55
Batog
Khim. Geterotsikl. Soedin., 2000
55.
L. V. Batog, V. Yu. Rozhkov, Yu. V. Khropov, N. V. Pyatakova, O. G. Busirgina, I. S. Severina and N. N. Makhova, RU Pat., no. 2158265, 2000.(Chem. Abstr., 2002, 136, 401763).
56.
Seregin I.V., Ovchinnikov I.V., Makhova N.N., Lyubetsky D.V., Lyssenko K.A.
Mendeleev Communications, 2003
57.
N. N. Makhova, Yu. S. Syroeshkina, V. V. Kuznetsov and V. Yu. Petukhova, Book of Abstracts of the International Conference ‘New Directions in the Chemistry of Heterocyclic Compounds’, Kislovodsk, Russia, 2009, p. 79.
59.
A new reaction of 1,2-di- and 1,2,3-trialkyldiaziridines: Ring expansion under the action of diethyl acetylenedicarboxylate in ionic liquids
Syroeshkina Y.S., Kuznetsov V.V., Kachala V.V., Makhova N.N.
Journal of Heterocyclic Chemistry, 2009
60.
61.
10.1016/j.mencom.2010.03.001_bib62
Syroeshkina
Izv. Akad. Nauk., Ser. Khim., 2009
62.
Syroeshkina Y.S., Kuznetsov V.V., Struchkova M.I., Epishina M.A., Makhova N.N.
Mendeleev Communications, 2008
63.
Syroeshkina Y.S., Kachala V.V., Ovchinnikov I.V., Kuznetsov V.V., Nelyubina Y.V., Lyssenko K.A., Makhova N.N.
Mendeleev Communications, 2009
64.
T. Nalesnik, WO Pat. 02/099018 A1.(Chem. Abstr., 2003, 138, 2661).
65.
Diazenium cations. 3. Formation and oxidation of a cis-trialkylhydrazine: cis-azomethinimines
Snyder J.P., Heyman M., Gundestrup M.
Journal of Organic Chemistry, 1978
67.
10.1016/j.mencom.2010.03.001_bib68
Bucala
Diabetes Rev., 1995
68.
B. Kurosu, JP Pat. 51133265 (A).(Chem. Abstr., 1977, 85, 63065a).
69.
B. L.Walworth, US Pat. 4091106 (A).(Chem. Abstr., 1978, 86, 16667j).
70.
V. R. Akhmetova, G. R. Nadyrgulova, S. R. Khafizova, R. V. Kunakova, T. V. Tjumkina and U. M. Dzhemilev, RU Pat. 2291149 C1.(Chem. Abstr., 2007, 146, 142693).
72.
Zum 1,3-dipolarophilen Reaktionsverhalten des Äthylentetracarbonitrils
Burger K., Schickaneder H., Pinzel M.
European Journal of Organic Chemistry, 1976
73.
Zum Mechanismus der „criss-cross”-Cycloaddition
Burger K., Thenn W., Rauh R., Schickaneder H., Gieren A.
European Journal of Inorganic Chemistry, 1975
74.
Novel heterocycles containing the pyrazole unit
Světlík J., Liptaj T.
Journal of the Chemical Society Perkin Transactions 1, 2002
75.
10.1016/j.mencom.2010.03.001_bib76
Putilova
Zh. Org. Khim., 2005
76.
10.1016/j.mencom.2010.03.001_bib77
Putilova
Zh. Org. Khim., 2006
77.
Small Molecule Inhibitor of Mitotic Spindle Bipolarity Identified in a Phenotype-Based Screen
Mayer T.U., Kapoor T.M., Haggarty S.J., King R.W., Schreiber S.L., Mitchison T.J.
Science, 1999
78.
Dissecting cellular processes using small molecules: identification of colchicine-like, taxol-like and other small molecules that perturb mitosis
Haggarty S.J., Mayer T.U., Miyamoto D.T., Fathi R., King R.W., Mitchison T.J., Schreiber S.L.
Chemistry & Biology, 2000
79.
In Vitro and in Vivo Evaluation of Dihydropyrimidinone C-5 Amides as Potent and Selective α1A Receptor Antagonists for the Treatment of Benign Prostatic Hyperplasia
Barrow J.C., Nantermet P.G., Selnick H.G., Glass K.L., Rittle K.E., Gilbert K.F., Steele T.G., Homnick C.F., Freidinger R.M., Ransom R.W., Kling P., Reiss D., Broten T.P., Schorn T.W., Chang R.S., et. al.
Journal of Medicinal Chemistry, 2000
80.
10.1016/j.mencom.2010.03.001_bib81
Putilova
Izv. Akad. Nauk, Ser. Khim., 2005
82.
I. Yamatsu, T. Suzuki, S. Abe, Y. Inai, Y. Suzuki and O. Tagaya, Ger. Offen. DE 3320544.(Chem. Abstr., 1984, 101, 7482).
83.
K. Nakamoto, T. Suzuki, S. Abe, K. Hayashi, A. Kajiwara, I. Yamatsu, I. Otsuka and H. Shiojiri, Eur. Pat. Appl. EP 0194693.(Chem. Abstr., 1989, 111, 5730).
84.
I. Yamatsu, T. Suzuki, S. Abe, K. Nakamoto, A. Kajiwara, T. Fujimori, K. Harada and S. Kitamura, Eur. Pat. Appl. EP 110397.(Chem. Abstr., 1985, 102, 6974).
85.
Solvent-Free Synthesis of γ-Nitroketones and γ-Nitroesters Promoted by the Ionic Liquid/K2CO3 Catalytic System
Zlotin S., Bogolyubov A., Kryshtal G., Zhdankina G., Struchkova M., Tartakovsky V.
Synthesis, 2006
86.
10.1016/j.mencom.2010.03.001_bib87
Zlotin
Izv. Akad. Nauk, Ser. Khim., 2007
88.
Regio-, stereo-, and enantioselective reactions of carbon acids catalyzed by recoverable organic catalysts bearing ionic liquid moieties
Zlotin S.G., Kryshtal G.V., Zhdankina G.M., Kucherenko A.S., Bogolyubov A.V., Siyutkin D.E.
Pure and Applied Chemistry, 2009
89.
Enantioselective Organocatalysis, ed. P. I. Dalko, Wiley-VCH, Weinheim, 2007, p. 536.
90.
Asymmetric Organocatalysis: From Infancy to Adolescence
Dondoni A., Massi A.
Angewandte Chemie - International Edition, 2008
91.
Organocatalysis of asymmetric aldol reaction. Catalysts and reagents
Zlotin S.G., Kucherenko A.S., Beletskaya I.P.
Russian Chemical Reviews, 2009
92.
Organocatalysis—after the gold rush
Bertelsen S., Jørgensen K.A.
Chemical Society Reviews, 2009
93.
Asymmetric Enamine Catalysis
Mukherjee S., Yang J.W., Hoffmann S., List B.
Chemical Reviews, 2007
94.
Asymmetric organocatalysis
Pellissier H.
Tetrahedron, 2007
95.
Enantioselective organocatalysis
Gaunt M.J., Johansson C.C., McNally A., Vo N.T.
Drug Discovery Today, 2007
97.
Recyclable Stereoselective Catalysts
Trindade A.F., Gois P.M., Afonso C.A.
Chemical Reviews, 2009
100.
Supported Ionic Liquids. New Recyclable Materials for theL-Proline-Catalyzed Aldol Reaction
Gruttadauria M., Riela S., Aprile C., Meo P., D'Anna F., Noto R.
Advanced Synthesis and Catalysis, 2006
102.
Starodubtseva E.V., Turova O.V., Vinogradov M.G., Ferapontov V.A., Razmanov I.V., Zlotin S.G., Kucherenko A.S.
Mendeleev Communications, 2007
104.
The Ion Tag Strategy as a Route to Highly Efficient Organocatalysts for the Direct Asymmetric Aldol Reaction
Lombardo M., Easwar S., Pasi F., Trombini C.
Advanced Synthesis and Catalysis, 2009
106.
Functionalized ionic liquids catalyzed direct aldol reactions
Luo S., Mi X., Zhang L., Liu S., Xu H., Cheng J.
Tetrahedron, 2007
108.
Functionalized Chiral Ionic Liquids as Highly Efficient Asymmetric Organocatalysts for Michael Addition to Nitroolefins
Luo S., Mi X., Zhang L., Liu S., Xu H., Cheng J.
Angewandte Chemie - International Edition, 2006
112.
A modular approach to catalyst hydrophobicity for an asymmetric aldol reaction in a biphasic aqueous environment
Lombardo M., Easwar S., De Marco A., Pasi F., Trombini C.
Organic and Biomolecular Chemistry, 2008
114.
Water in Stereoselective Organocatalytic Reactions
Gruttadauria M., Giacalone F., Noto R.
Advanced Synthesis and Catalysis, 2009
118.
10.1016/j.mencom.2010.03.001_bib120
Siyutkin
Izv. Akad. Nauk, Ser. Khim., 2009
120.
Iminium Catalysis
Erkkilä A., Majander I., Pihko P.M.
Chemical Reviews, 2007
123.
The Catalytic Asymmetric Aldol Reaction
Machajewski T.D., Wong C.
Angewandte Chemie - International Edition, 2000
124.
10.1016/j.mencom.2010.03.001_bib126
Whalen
Aldrich. Acta, 2006
125.
CONCENTRATES
Chemical & Engineering News, 2003
126.
Chemical Footnote
RITTER S.K.
Chemical & Engineering News, 2008