New Development of the Solvent-Free Michael Addition

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (6): 600-608. Previous Articles Next Articles

无溶剂Michael加成反应的新进展

卢刚, 张谦, 许佑君^*

沈阳药科大学制药工程学院沈阳 110016

收稿日期:2003-08-07 修回日期:2003-11-06 接受日期:2004-02-01 发布日期:2022-09-21
通讯作者: ^*E-mail:xuyouju@mail.sy.ln.cn

New Development of the Solvent-Free Michael Addition

LU, Gang, ZHANG, Qian, XU, You-Jun^*

College of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016

Received:2003-08-07 Revised:2003-11-06 Accepted:2004-02-01 Published:2022-09-21

Abstract

Due to its excellent yield, high selectivity, convenient operation and cost-effectiveness, the echo-friendly reaction of the solvent-free Michael addition has been extensively explored recently. Some new synthetic methods have been achieved by employing various highly efficient catalysts, which will definitely broaden the application of this reaction. Recent development of solvent-free Michaeladdition is reviewed in this paper. Many successful instances are discussed indetail, which are prompted by basic, acidic catalysts or even under catalyst-free conditions.

Key words: solvent-free, Michael addition, catalyst

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LU, Gang, ZHANG, Qian, XU, You-Jun. New Development of the Solvent-Free Michael Addition[J]. Chinese Journal of Organic Chemistry, 2004, 24(6): 600-608.

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1 Nagendrappa, G. Resonance 2002,10, 59.
2 Komatsu, K. Kikan Kagaku Sosetsu 2000, 47, 163.
3 Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
4 Metzger, J. O. Angew. Chem., Int. Ed. Engl. 1998,37, 2975.
5 Li, X.-L.; Wang, Y.-M.; Meng, J.-B. Chin. J. Org. Chem.1998, 18, 20 (in Chinese).
(李晓陆, 王永梅, 孟继本, 有机化学, 1998, 18, 20.)
6 Bergmann, E. D.; Ginsberg, D.; Pappo, R. Org. React. 1959, Vol. X, 179.
7 Xu, Y. J.; Ohori, K.; Ohshima, T.; Shibasaki, M. Tetrahedron2002, 58, 2585.
8 Ohshima, T.; Xu, Y. J.; Takita, R.; Shimisu, S.; Zhong, D.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14546.
9 Cave, G. W. V.; Raston, C. L. J. Chem. Soc., Chem. Commun.2000, 2199.
10 Cave, G. W. V.; Raston, C. L.; Scott, J. L. J. Chem. Soc., Chem. Commun. 2001, 2159.
11 Cave, G. W. V.; Raston, C. L. J. Chem. Soc., Perkin Trans. 1 2001, 3258.
12 Liu, W. Y.; Xu, Q. H.; Liang, Y. M.; Chen, B. H,; Liu, W. M.; Ma, Y. X.J. Organomet. Chem. 2001, 637, 719.
13 Kayama, H.; Fujiwara, Y.; Kojima, K.; Nagata, C. Nippon Kagaku Kaishi 1998, (4), 252.
14 Patonay, T.; Varma, R. S.; Vass, A.; Levai, A.; Dudas, J. TetrahedronLett. 2001, 42, 1403.
15 Grossman, R. B.; Comesse, S.; Rasne, R. M.; Hattori, K.; Delong, M. N.J. Org. Chem. 2003, 68, 871.
16 Michaud, D.; Hamelin, J.; Texier-Boullet, F.; Toupet, L. Tetrahedron 2002, 58, 5865.
17 Ballini, R.; Marziali, P.; Mozzicafreddo, A. J. Org. Chem. 1996, 61, 3209.
18 Ballini, R.; Bosica, G.; Fiorini, D. Tetrahedron Lett. 2001, 42, 8471.
19 Ballini, R.; Bosica, G.; Livi, D.; Palmieri, A.; Maggi, R.; Sartori, G.Tetrahedron Lett. 2003, 44, 2271.
20 Rissafi, B.; El Louzi, A.; Loupy, A.; Petit, A.; Soufiaoui, M.; Tetouani, S. F. Eur. J. Org. Chem. 2002, 2518.
21 Diez-Barra, E.; delaHoz, A.; Merino, S.; SanchezVerdu, P. Tetrahedron Lett. 1997, 38, 2359.
22 Loupy, A.; Zaparucha, A. Tetrahedron Lett. 1993, 34, 473.
23 Mirza-Aghayan, M.; EtemadMoghadm, G.; Zaparucha, A.; Berlan, J.; Loupy, A.; Koenig, M. Tetrahedron: Asymmetry 1995, 6, 2643.
24 Ishikawa, T.; Araki, Y.; Kumamoto. T.; Seki, H.; Fukuda, K.; Isobe, T.Chem. Commun. 2001, 245.
25 Perrard, T.; Plaquevent, J. C.; Desmurs, J. R.; Hebrault, D. Org. Lett. 2000, 2, 2959.
26 Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J. C.; Cahard, D.Synthesis 2001, 1742.
27 Kotsuki, H.; Arimura, K.; Ohishi, T.; Maruzasa, R. J. Org. Chem. 1999, 64, 3770.
28 Christoffers, J. J. Chem. Soc., Chem. Commun. 1997, 943.
29 Christoffers, J. Synlett 2001, 723.
30 Kotsuki, H.; Arimura, K. Tetrahedron Lett. 1997, 38, 7583.
31 Boruah, A.; Baruah, M.; Prajapati, D.; Sandhu, J. S. Synth. Commun.1998, 28, 653.
32 Bartoli, G.; Bosco, M.; Bellucci, M. C.; Marcantoni, E.; Sambri, L.; Toregiani, E. Eur. J. Org. Chem. 1999, 617.
33 Ranu, B. C.; Hajra, A.; Jana, U. Tetrahedron Lett. 2000,41, 531.
34 Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813.
35 Yadav, J. S.; Geetha, V.; Reddy, B. V. S. Synth. Commun. 2002, 32, 3519.
36 Soriente, A.; Spinella, A.; DeRosa, M.; Giordano, M.; Scettri, A. Tetrahedron Lett. 1997, 38, 289.
37 Baruah, B.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1997, 38, 1449.
38 Kayama, H.; Sawaguchi, M.; Nagata, C. Nippon Kagaku Kaishi 1999, 2, 145.
39 Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.;Mathe, D. Synthesis 1998, 1213.
40 Varma, R. S.; Saini, R. K. Synlett 1997, 857.
41 Avalos, M.; Babiano, R.; Bravo, J. L.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Tetrahedron Lett. 1998, 39, 9301.
42 Ranu, B. C.; Hajra, A.; Jana, U. Synlett 2000, 75.
43 Ranu, B. C.; Hajra, A. Tetrahedron 2001, 57,4767.
44 Li, X.-L.; Wang, Y.-M.; Matsuura, T.; Meng, J.-B. J. Heterocycl.Chem. 1999, 36, 697.
45 Kaupp, G.; Naimi-Jamal, M. R.; Schmeyers, J. Tetrahedron 2003, 59, 3753.
46 Ranu, B. C.; Dey, S. S.; Hajra, A. Arkivoc 2002, Part 7, 76.
47 Romanova, N. N.; Gravis, A. G.; Leshcheva, I. F.; Bundel, Y. G. Mendeleev Commun. 1998, (4), 147.

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无溶剂Michael加成反应的新进展

New Development of the Solvent-Free Michael Addition

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