Citation: Sanjoy Keithellakpam, Warjeet S. Laitonjam. A simple, efficient and green procedure for Michael addition catalyzed by [C4dabco]OH ionic liquid[J]. Chinese Chemical Letters, ;2014, 25(05): 767-770. doi: 10.1016/j.cclet.2014.01.032
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A dabco-based basic ionic liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane hydroxide, has been developed as a catalyst for a convenient and rapid method for the Michael addition of active methylene compounds to α,β-unsaturated carboxylic esters and nitriles. The method is very simple, and the yields are very high. The catalyst can be recycled several times without much loss of activity.
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Keywords:
- Dabco-based,
- Ionic liquid,
- Michael addition,
- Recyclable
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[1]
[1] (a) T. Welton, Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev. 99 (1999) 2071-2084; (b) P. Wassercheid, W. Keim, Ionic liquids-new "solutions" for transition metal catalysis, Angew. Chem. Int. Ed. 39 (2000) 3772-3789; (c) R. Sheldon, Catalytic reactions in ionic liquids, Chem. Commun. (2001) 2399-2407; (d) J. Dupont, R.F. de Souza, P.A.Z. Suarez, Ionic liquid (molten salt) phase organometallic catalysis, Chem. Rev. 102 (2002) 3667-3692; (e) P. Wassercheid, T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2002.
-
[2]
[2] J.A. Boon, J.A. Levisky, J.L. Pflug, J.S. Wilkes, Friedel-Crafts reactions in ambienttemperature molten salts, J. Org. Chem. 51 (1986) 480-483.
-
[3]
[3] J.R. Harjani, S.J. Nara, M.M. Salunkhe, Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation, Tetrahedron Lett. 43 (2002) 1127-1130.
-
[4]
[4] (a) J. Fraga-Dubreuil, K. Bourahla, M. Rahmouni, J.P. Bazureau, J. Hamelin, Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media, Catal. Commun. 3 (2002) 185-190; (b) H. Xing, T. Wang, Z.H. Zhou, Y. Dai, Novel Brønsted-acidic ionic liquids for esterifications, Ind. Eng. Chem. Res. 44 (2005) 4147-4150; (c) J. Gui, X. Cong, D. Liu, et al., Novel brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification, Catal. Commun. 5 (2004) 473-477; (d) H.P. Zhu, F. Yang, J. Tang, M.Y. He, Brønsted acidic ionic liquid 1-methylimidazolium tetrafluoroborate: a green catalyst and recyclable medium for esterification, Green Chem. 5 (2003) 38-39.
-
[5]
[5] (a) G. Driver, K.E. Johnson, 3-Methylimidazolium bromohydrogenates(I): a roomtemperature ionic liquid for ether cleavage, Green Chem. 5 (2003) 163-169; (b) G.J. Kemperman, T.A. Roeters, P.W. Hilberink, Cleavage of aromatic methyl ethers by chloroaluminate ionic liquid reagents, Eur. J. Org. Chem. 9 (2003) 1681-1686.
-
[6]
[6] (a) P. Formentin, H. Garcia, A. Leyva, Assessment of the suitability of imidazolium ionic liquids as reaction medium for base-catalysed reactions: case of Knoevenagel and Claisen-Schmidt reactions, J. Mol. Catal. A: Chem. 214 (2004) 137-142; (b) H. Chen, D.R. Justes, R.G. Cooks, Proton affinities of N-heterocyclic carbene super bases, Org. Lett. 7 (2005) 3949-3952.
-
[7]
[7] (a) J.K. Myers, E.N. Jacobsen, Asymmetric synthesis of b-amino acid derivatives via catalytic conjugate addition of hydrazoic acid to unsaturated imides, J. Am. Chem. Soc. 121 (1999) 8959-8960; (b) J.S. Yadav, B.V.S. Reddy, G. Baishya, Green protocol for conjugate addition of thiols to α,β-unsaturated ketones using a [Bmim]PF6/H2O system, J. Org. Chem. 68 (2003) 7098-7100; (c) N. Azizi, M.R. Saidi, LiClO4 accelerated Michael addition of amines to a, b-unsaturated olefins under solvent-free conditions, Tetrahedron 60 (2004) 383-387.
-
[8]
[8] (a) E.D. Bergmann, D. Ginsburg, R. Pappo, Organic Reactions, vol. 10, John Wiley & Sons, New York, 1959, p. 179; (b) S. Kobayashi, Rare earth metal trifluoromethanesulfonates as water-tolerant Lewis acid catalysts in organic synthesis, Synlett 9 (1994) 689-701; (c) N. Srivastava, B.K. Banik, Bismuth nitrate-catalyzed versatile Michael reactions, J. Org. Chem. 68 (2003) 2109-2114.
-
[9]
[9] (a) L. Yang, L.W. Xu, C.G. Xia, Highly efficient KF/Al2O3-catalyzed versatile hetero- Michael addition of nitrogen, oxygen, and sulfur nucleophiles to α,β-ethylenic compounds, Tetrahedron Lett. 46 (2005) 3279-3282; (b) D.Y. Kim, S.C. Huh, S.M. Kim, Enantioselective Michael reaction of malonates and chalcones by phase-transfer catalysis using chiral quaternary ammonium salt, Tetrahedron Lett. 42 (2001) 6299-6301; (c) A. Horvath, Catalysis and regioselectivity in the Michael addition of azoles. Kinetics vs. thermodynamic control, Tetrahedron Lett. 37 (1996) 4423-4426; (d) K. Shimizu, M. Miyagi, T. Kan-no, T. Kodama, Y. Kitayama, Fe3+-exchanged fluorotetrasilicic mica as an active and reusable catalyst for Michael reaction, Tetrahedron Lett. 44 (2003) 7421-7424; (e) B. Ni, Q. Zhang, A.D. Headley, Functionalized chiral ionic liquid as recyclable organocatalyst for asymmetric Michael addition to nitrostyrenes, Green Chem. 9 (2007) 737-739; (f) M.M. Dell'Anna, V. Gallo, P. Mastrorilli, et al., Metal catalysed Michael additions in ionic liquids, Chem. Commun. (2002) 434-435; (g) X. Xin, X. Guo, H.F. Duan, Y. Lin, H. Sun, Efficient Knoevenagel condensation catalyzed by cyclic guanidiniumlactate ionic liquid as medium, Catal. Commun. 8 (2007) 115-117; (h) G.A. Salvador, S. Hasegawa, M. Hirano, S. Komiya, Michael reaction promoted byη1-o-enolatoruthenium(Ⅱ) complexes derived from Ru(cod)(cot), diphosphine, and dimethyl malonate, Tetrahedron Lett. 39 (1998) 5209-5212.
-
[10]
[10] B.C. Ranu, B. Subhash, 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 (2005) 3049-3052.
-
[11]
[11] Y. Yu, L.B. Wang, Z. Zhang, et al., [Bmim]OAc catalyzed Michael addition of active methylene to α,β-unsaturated carboxylic esters and nitriles, Chem. Res. Chin. Univ. 26 (2010) 554-557.
-
[12]
[12] Y. Yang, S.X. Dong, X.H. Liu, L.L. Lin, X.M. Feng, Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of a, b-unsaturated γ-butyrolactams with alkylidene malonates, Chem. Commun. 48 (2012) 5040-5042.
-
[13]
[13] Z.Z. Yang, L.N. He, X.Y. Dou, S. Chanfreau, Dimethyl carbonate synthesis catalyzed by DABCO-derived basic ionic liquids via transesterification of ethylene carbonate with methanol, Tetrahedron Lett. 51 (2010) 2931-2934.
-
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