Reviews

Research Progress in the Environmentally-Friendly Michael Addition

  • Li Zhifeng ,
  • Hou Hailiang ,
  • Ying Anguo ,
  • Xu Songlin
Expand
  • a. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072;
    b. School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000

Received date: 2013-12-30

  Revised date: 2014-01-26

  Online published: 2014-02-14

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21106090, 21176170).

Abstract

Michael addition is one kind of important reaction in the organic field. With the enhancement of environmental awareness and the depth of green chemistry research, environmentally-friendly Michael addition has made many successes. The research progress over the past 5 years in the Michael addition involving ionic liquids, enzyme catalysis, solid phase supported catalysis and polyethylene glycol (PEG) is reviewed. This paper is consisted of six parts, focusing on the efficiency of the reaction system, the probable catalytic mechanism and the recycle of the catalyst. In the first part, a brief introduction is given. Then the Michael addition used the ionic liquid as catalyst or/and solvent is elaborated. In this part, acidic ionic liquid, basic ionic liquids and chiral ionic liquid are described, respectively. As a mild catalyst, enzymes are described in the third part. The solid phase supported catalysis has been used in many reaction without exception to Michael addition. So, in the fourth part, the catalysts of polymer supported, silica-supported and superparamagnetic nano supported are stated. Following, the successful use of polyethylene glycol (PEG) as a green solvent is presented. Finally, the conclusion, the existing problems of these green technologies and the prospect are summarized.

Cite this article

Li Zhifeng , Hou Hailiang , Ying Anguo , Xu Songlin . Research Progress in the Environmentally-Friendly Michael Addition[J]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1074 -1091 . DOI: 10.6023/cjoc201312034

References

[1] Perlmutter, P. Conjugate Addition in Organic Synthesis, Pergamon, Oxford, 1992.
[2] Kotsuki, H.; Arimura, K.; Ohishi, T.; Maruzasa, R. J. Org. Chem. 1999, 64, 3770.
[3] Dupont, J.; Souza, R. F.; Suarez, P. A. Chem. Rev. 2002, 102, 3667.
[4] Olivier-Bourbigou, H.; Magna, L.; Morvan, D. Appl. Catal. A: Gen. 2010, 373, 1.
[5] Guo, H.; Li, X.; Wang, J. L.; Jin, X. H.; Lin, X. F. Tetrahedron 2010, 66, 8300.
[6] Kumar, A.; Srivastava, S.; Gupta, G.; Kumara, P.; Sarkarb, J. RSC Adv. 2013, 3, 3548.
[7] Vessieres, A.; Top, S.; Pigeon, P.; Hillard, E.; Boubeker, L.; Spera, D.; Jaouen, G. J. Med. Chem. 2005, 48, 3937.
[8] Chelghoum, M.; Bahnous, M.; Bouraiou, A.; Bouacida, S.; Belfaitah, A. Tetrahedron Lett. 2012, 53, 4059.
[9] Jiang, X. Y.; Ye, W. D.; Song, X. H.; Ma, W. X.; Lao, X. J.; Shen, R. P. Int. J. Mol. Sci. 2011, 12, 7438.
[10] Dabiri, M.; Salehi, P.; Bahramnejad, M.; Baghbanzadeh, M. Monatsh. Chem. 2012, 143, 109.
[11] Bedos, P.; Amblard, M.; Subra, G.; Dodey P.; Luccarini, J. M.; Paquet, J. L.; Pruneau, D.; Aumelas, A.; Martinez, J. J. Med. Chem. 2000, 43, 2387.
[12] Han, F.; Yang, L.; Li, Z.; Xia, C. G. Org. Biomol. Chem. 2012, 10, 346.
[13] Narayanaperumal, S.; Silva, R. C.; Feu, K. S.; Torre, A. F.; Corrêa, A. G.; Paix, M. W. Ultrason. Sonochem. 2013, 20, 793.
[14] Sarda, S. R.; Jadhav, W. N.; Shete, A. S.; Dhopte, K. B.; Sadawarte, S. M.; Gadge, P. J.; Pawar, R. P. Synth. Commun. 2010, 40, 2178.
[15] (a) Edmonson, S.; Danishefsky, S. J.; Lorenzino, L.; Rosen, N. J. J. Am. Chem. Soc. 1999, 121, 2147.
(b) Dandia, A.; Singh, R.; Merienne, C.; Morgant, G.; Loupy, A. Sulfur Lett. 2003, 26, 201.
[16] Siddiqui, I. R.; Shamim, S.; Abumhdi, A. A.; Waseem, M. A.; Srivastava, A. New J. Chem. 2013, 37, 1258
[17] Ying, A. G.; Liu, L.; Wu, G. F.; Chen, G.; Chen, X. Z.; Ye, W. D. Tetrahedron Lett. 2009, 50, 1653.
[18] Ying, A. G.; Chen, X. Z.; Wu, C. L.; Zheng, R. H.; Liang, H. D.; Ge, C. H. Synth. Commun. 2012, 42, 3455.
[19] Ying, A. G.; Wang, L. M.; Deng, H. X.; Chen, J. H.; Chen, X. Z.; Ye, W. D. ARKIVOC 2009, xi, 288.
[20] Ying, A. G.; Zheng, M.; Xu, H. D.; Qiu, F. L.; Ge, C. H. Res. Chem. Intermed. 2011, 37, 883.
[21] Truong, T. K. T.; Vo-Thanh, G. Tetrahedron 2010, 66, 5277.
[22] Ni, B.; Zhang, Q. Y.; Headley, A. D. Green Chem. 2007, 9, 737.
[23] Ni, B.; Zhang, Q. Y.; Dhungana, K.; Headley, A. D. Org. Lett. 2009, 11, 1037.
[24] Zheng, Z. L.; Perkins, B. L.; Ni, B. J. Am. Chem. Soc. 2010, 132, 50.
[25] Wang, W. H.; Wang, X. B.; Kodama, K.; Hirose, T.; Zhang, G. Y. Tetrahedron 2010, 66, 497.
[26] (a) Hayashi, Y.; Toyoshima, M.; Gotoh, H.; Ishikawa, H. Org. Lett. 2009, 11, 45.
(b) Rueping, M.; Kuenkel, A.; Tato, F.; Bats, J. W. Angew. Chem., Int. Ed. 2009, 48, 3699.
(c) Landa, A.; Maestro, M.; Masdeu, C.; Puente, A.; Vera, S.; Oiarbide, M.; Palomo, C. Chem. Eur. J. 2009, 15, 1562.
[27] Maltsev, O. V.; Kucherenko, A. S.; Zlotin, S. G. Eur. J. Org. Chem. 2009, 5134.
[28] Ozoe, Y.; Mochida, K.; Yagi, K.; Nakamura, M.; Akamatsu, M.; Miyake, T.; Matsumura, F. Pest. Biochem. Phys. 2000, 66, 92.
[29] (a) Parker, C. A.; Matthews, J. C.; Gunn, R. N.; Martarello, L.; Cunningham, V. J.; Dommett, D.; Knibb, S. T.; Bender, D.;. Jakobsen, S.; Brown, J.; Gee, A. D. Synapse 2005, 55, 270.
(b) Frampton, J. E.; Foster, R. H. CNS Drugs 2006, 20, 685.
(c) Dambrova, M.; Zvejniece, L.; Liepinsh, E.; Cirule, H.; Zharkova, O.; Veinberg, G.; Kalvinsh, I. Eur. J. Pharm. 2008, 583, 128.
[30] Maltsev, O. V.; Kucherenko, A. S.; Beletskaya, I. P.; Tartakovsky, V. A.; Zlotin, S. G. Eur. J. Org. Chem. 2010, 2927.
[31] Zaks, A.; Klibanov, A. M. Science 1984, 224, 1249.
[32] Kitazume, T.; Ikeya, T.; Murata, K. J. Chem. Soc., Chem. Commun. 1986, 1331.
[33] Franke, D.; Machajewski, T.; Hsu, C. C.; Wong, C. H. J. Org. Chem. 2003, 68, 6828.
[34] Lidia, M.; Małgorzata, K.; Tomasz, C.; Piotr, K. J. Mol. Catal. B: Enzym. 2012, 81, 25.
[35] Chen, X. Y.; Liang, Y. R.; Xu, F. L.; Wu, Q.; Lin, X. F. J. Mol. Catal. B: Enzym. 2013, 97, 18.
[36] (a) Cai, Y.; Wu, Q.; Xiao, Y. M.; Lv, D. S.; Lin, X. F. J. Biotechnol. 2006, 121, 330.
(b) Xu, J. M.; Yao, S. P.; Wu, W. B.; Lv, D. S.; Lin, X. F. J. Mol. Catal. B: Enzym. 2005, 35, 122.
(c) Qian, C.; Xu, J. M.; Wu, Q.; Lv, D. S.; Lin, X. F. Tetrahedron Lett. 2007, 48, 6100.
[37] Wang, J. L.; Xu, J. M.; Wu, Q.; Lv, D. S.; Lin, X. F. Tetrahedron 2009, 65, 2531.
[38] Liu, Z. Q.; Liu, B. K.; Wu, Q.; Lin, X. F. Tetrahedron 2011, 67, 9736.
[39] (a) Li, Q.; Mitscher, L. A.; Shen, L. L. Med. Res. Rev. 2000, 20, 231.
(b) Nagarajan, M.; Xiao, X. S.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. J. Med. Chem. 2003, 46, 5712.
[40] Xie, B. H.; Guan, Z.; He, Y. H. J. Chem. Technol. Biotechnol. 2012, 87, 1709.
[41] Cai, J. F.; Guan, Z.; He, Y. H. J. Mol. Catal. B: Enzym. 2011, 68, 240.
[42] Xu, K. L.; Guan, Z.; He, Y. H. J. Mol. Catal. B: Enzym. 2011, 71, 108.
[43] Geertsema, E. M.; Miao, Y. F.; Tepper, P. G.; Haan, P.; Zandvoort, E.; Poelarends, G. J. Chem. Eur. J. 2013, 19, 14407.
[44] Hertweck, C. Angew. Chem., Int. Ed. 2009, 48, 4688.
[45] Jin, J. F.; Oskam, P. C.; Karmee, S. K.; Straathofb, A. J.; Hanefeld, U. Chem. Commun. 2010, 46, 8588.
[46] de Souza, R. O.; Matos, L.; Goncalves, K. M.; Costa, I. C.; Babics, I.; Leite, S. G.; Oestreicher, E. G.; Antunes, O. A. C. Tetrahedron Lett. 2009, 50, 2017.
[47] (a) Cozzi, F. Adv. Synth. Catal. 2006, 348, 1367.
(b) Gruttadauria, M.; Giacalone, F.; Noto, R. Chem. Soc. Rev. 2008, 37, 1666.
[48] Tuchman-Shukrona, L.; Portnoy, M. Adv. Synth. Catal. 2009, 351, 541.
[49] Wiesner, M.; Neuburger, M.; Wennemers, H. Chem. Eur. J. 2009, 15, 10103.
[50] Lalonde, M. P.; Chen, Y.; Jacobsen, E. N. Angew. Chem. 2006, 118, 6514.
[51] Tuchman-Shukron, L.; Miller, S. J.; Portnoy, M. Chem. Eur. J. 2012, 18, 2290.
[52] Yalalov, D. A.; Tsogoeva, S. B.; Schmatz, S. Adv. Synth. Catal. 2006, 348, 826.
[53] (a) Luo, S.; Mi, X.; Zhang, L.; Liu, S.; Xu, H.; Cheng, J. P. Angew. Chem. 2006, 118, 3165.
(b) Zu, L.; Wang, J.; Li, H.; Wang, W. Org. Lett. 2006, 8, 3077.
[54] (a) Lattanzi, A. Chem. Commun. 2009, 1452.
(b) Palomo, C.; Mielgo, A. Angew. Chem. 2006, 118, 8042.
[55] Alza, E.; Perics, M. A. Adv. Synth. Catal. 2009, 351, 3051.
[56] Liu, J.; Li, P. H.; Zhang, Y. C.; Ren, K.; Wang, L.; Wang, G. W. Chirality 2010, 22, 432.
[57] (a) Li, C. J. Chem. Rev. 2005, 105, 3095.
(b) Zhu, S. L.; Yu, S. Y.; Ma, D. W. Angew. Chem., Int. Ed. 2008, 47, 545.
[58] Chuan, Y. M.; Chen, G. H.; Peng, Y. G. Tetrahedron Lett. 2009, 50, 3054.
[59] (a) Ballini, R.; Bosica, G.; Livi, D.; Palmieri, A.; Maggi, R.; Sartori, G. Tetrahedron Lett. 2003, 44, 2271.
(b) Macquarrie, D. J.; Maggi, R.; Mazzacani, A.; Sartori, G.; Sartorio, R. Appl. Catal. A: Gen. 2003, 246, 183.
(c) Hamaya, J.; Suzuki, T.; Hoshi, T.; Shimizu, K. I.; Kitayama, Y.; Hagiwara, H. Synlett 2003, 873.
[60] Sobhani, S.; Parizi, Z. P.; Rezazadeh, S. J. Organomet. Chem. 2011, 696, 813.
[61] Jain, S. L.; Modakb, A.; Bhaumik, A. Green Chem. 2011, 13, 586.
[62] Zhao, Y. B.; Zhang, L. W.; Wu, L. Y.; Zhong, X.; Li, R.; Ma, J. T. Tetrahedron: Asymmetry 2008, 19, 1352.
[63] Li, P. H.; Wang, L.; Zhang, Y. C.; Wang, G. W. Tetrahedron 2008, 64, 7633.
[64] Saidi, M. R.; Pourshojaei, Y.; Aryanasab, F. Synth. Commun. 2009, 39, 1109.
[65] Wang, B. G.; Ma, B. C.; Wang, Q.; Wang, W. Adv. Synth. Catal. 2010, 352, 2923.
[66] Riente, P.; Mendoza, C.; Pericas, M. A. J. Mater. Chem. 2011, 21, 7350.
[67] (a) Enders, D.; Saint-Dizier, A.; Lannou, M. I.; Lenzen, A. Eur. J. Org. Chem. 2006, 1, 29.
(b) Kulkarni, M. A.; Pandurangi, V. R.; Desai, U. V.; Wadgaonkar, P. P. C. R. Chim. 2012, 15, 745.
(c) Xu, Q.; Han, L. B. Org. Lett. 2006, 8, 2099.
[68] Massart, R.; Dubois, E.; Cabuil, V.; Hasmonay, E. J. Magn. Magn. Mater. 1995, 149, 1.
[69] Sobhani, S.; Bazrafshan, M.; Delluei, A. A.; Parizi, Z. P. Appl. Catal. A: Gen. 2013, 454, 145.
[70] Ridder, L.; Rietjens, I. M.; Vervoort, J.; Mulholland, A. J. J. Am. Chem. Soc. 2002, 124, 9926.
[71] Varma, R. S.; Polshettiwar, V. US 2011/0054180, 2011 [Chem. Abstr. 2011, 154, 283572].
[72] Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Green Chem. 2005, 7, 64.
[73] Wang, J. Q.; He, L. N.; Miao, C. X. Green Chem. 2009, 11, 1013.
[74] Liu, R. X.; Cheng, H. Y.; Wang, Q.; Wu, C. Y.; Ming, J.; Xi, C. Y.; Yu, Y. C.; Cai, S. X.; Zhao, F. Y. Green Chem. 2008, 10, 1082.
[75] Luo, C. C.; Zhang, Y. H.; Wang, Y. G. J. Mol. Catal. A: Chem. 2005, 229, 7.
[76] Andreae, M. R. M.; Davis, A. P. Tetrahedron: Asymmetry 2005, 16, 2487.
[77] Chandrasekhar, S.; Narsihmulu, C.; Saritha, B.; Sultana, S. S. Tetrahedron Lett. 2004, 45, 5865.
[78] Xu, D. Q.; Luo, S. P.; Wang, Y. F.; Xia, A. B.; Yue, H. D.; Wang, L. P.; Xu, Z. Y. Chem. Commun. 2007, 4393.
[79] Firouzabadi, H.; Iranpoor, N.; Abbasi, M. Tetrahedron 2009, 65, 5293.
[80] Kumar, D.; Patel, G.; Mishra, B. G.; Varma, R. S. Tetrahedron Lett. 2008, 49, 6974.
[81] Liang, J. Ph. D. Dissertation, Zhejiang University, Hangzhou, 2012 (in Chinese).
(梁军, 博士论文, 浙江大学, 杭州, 2012.)
[82] Chen, I. L.; Chang, K. M.; Miaw, C. L.; Liao, C. H.; Chen, J. J.; Wang, T. C. Bioorg. Med. Chem. 2007, 15, 6527.
[83] Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 21, 2015.
[84] Kumar, R.; Chaudhary, P.; Nimesh, S.; Chandra, R. Green Chem. 2006, 8, 356.
[85] Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.
[86] Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
[87] Kappe, C. O. Tetrahedron 1993, 49, 6937.
[88] Wang, X. C.; Quan, Z. J.; Zhang, Z. Tetrahedron 2007, 63, 8227.
[89] Chu, C. M.; Gao, S.; Sastry, M. N. V.; Kuo, C. W.; Lu, C.; Liu, J. T.; Yao, C. F. Tetrahedron 2007, 63, 1863.
[90] Kreilein, M. M.; Hofferberth, J. E.; Hart, A. C.; Paquette, L. A. J. Org. Chem. 2006, 71, 7329.
[91] Hanessian, S.; Roy, P. J.; Petrini, M.; Hodges, P. J.; Fabio, R. D.; Carganico, G. J. Org. Chem. 1990, 55, 5766.
[92] Chang, M. Y.; Lee, M. F.; Lee, N. C.; Huang, Y. P.; Lin, C. H. Tetrahedron Lett. 2011, 52, 588.
[93] Perin, G.; Borges, E. L.; Rosa, P. C.; Carvalho, P. N.; Lenard, E. J. Tetrahedron Lett. 2013, 54, 1718.
Outlines

/

〈 〉