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Polyguanidine as a Highly Efficient and Reusable Catalyst for Knoevenagel Condensation Reactions in Water
Xian-Liang
Zhao A C,
Ke-Fang
Yang B C,
Xuan-Gan
Liu A,
Chun-Lin
Ye A,
Li-Wen
Xu B and
Guo-Qiao
Lai B
A
School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, China.
B
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China.
C
Corresponding authors. Email: xlzhao@iccas.ac.cn; kfyang@iccas.ac.cn
Australian Journal of Chemistry
66(4)
500-504 http://dx.doi.org/10.1071/CH12507
Submitted: 15 November 2012 Accepted: 12 December 2012 Published:
24
January
2013
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Abstract
Polyguanidine is used as a novel and highly efficient catalyst in the Knoevenagel reaction of aldehydes with active methylene compounds in water to afford substituted electrophilic alkenes. This method is applicable for a wide range of aldehydes including aromatic and heterocyclic substrates. The polyguanidine catalyst can be recovered by simple filtration and reused many times for the aqueous Knoevenagel reaction without loss of activity. 
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References
[1]
(a) E. Knoevenagel, Ber. Dtsch. Chem. Ges. 1898, 31, 2585. | CrossRef | CAS |  (b) G. Jones, Org. React. 1967, 15, 204. (c) L. F. Tietze, Chem. Rev. 1996, 96, 115. | CrossRef | (d)
L. F. Tietze, U. Beifuss, in Comprehensive Organic Synthesis (Eds B. M. Trost, I. Fleming, C. H. Heathcock) 1991, Vol. 2, pp. 341–392 (Pergamon Press: Oxford). (e) F. Bigi, L. Chesini, R. Maggi, G. Sartori, J. Org. Chem. 1999, 64, 1033. | CrossRef | (f) N. Yu, J. M. Aramini, M. W. Germann, Z. Huang, Tetrahedron Lett. 2000, 41, 6993. | CrossRef |
[2]
G. Cardillo, S. Fabbroni, L. Gentilucci, M. Gianotti, A. Tolomelli, Synth. Commun. 2003, 33, 1587. | CrossRef | CAS |
[3]
W. Lehnert, Tetrahedron Lett. 1970, 11, 4723. | CrossRef |
[4]
F. Delgado, J. Tamariz, G. Zepeda, M. Landa, R. Miranda, J. Garcia, Synth. Commun. 1995, 25, 753. | CrossRef | CAS |
[5]
F. Texier-Boullet, A. Foucaud, Tetrahedron Lett. 1982, 23, 4927. | CrossRef | CAS |
[6]
Y. V. Subba Rao, D. E. De Vos, P. A. Jacobs, Angew. Chem. Int. Ed. 1977, 36, 2661.
[7]
(a) T. I. Reddy, R. S. Varma, Tetrahedron Lett. 1997, 38, 1721. | CrossRef | CAS | (b) Q. L. Wang, Y. D. Ma, B. Zuo, Synth. Commun. 1997, 27, 4107. | CrossRef |
[8]
(a) C. Su, Z.-C. Chen, Q. G. Zheng, Synthesis 2003, 555. | CAS | (b) J. R. Harjani, S. J. Nara, M. M. Salunkhe, Tetrahedron Lett. 2002, 43, 1127. | CrossRef | (c) D. W. Morrison, D. C. Forbes, J. H. Davis, Tetrahedron Lett. 2001, 42, 6053. | CrossRef | (d) F. A. Khan, J. Dash, R. Satapathy, S. K. Upadhyay, Tetrahedron Lett. 2004, 45, 3055. | CrossRef | (e) B. C. Ranu, R. Jana, Eur. J. Org. Chem. 2006, 3767. | CrossRef | (f) Y. O. Sharma, M. S. Degani, Green Chem. 2009, 11, 526. | CrossRef | (g) D. Z. Xu, Y. J. Liu, S. Shi, Y. M. Wang, Green Chem. 2010, 12, 514. | CrossRef |
[9]
A. Coelho, A. Crespo, F. Fernandez, P. Biagini, A. Stefanachi, E. Sotelo, Comb. Chem. High T. Scr. 2008, 11, 843. | CrossRef | CAS |
[10]
B. Tamami, A. Fadavi, Catal. Commun. 2005, 6, 747. | CrossRef | CAS |
[11]
P. Anastas, J. C. Warner, Green Chemistry: Theory and Practice 1998 (Oxford University Press: Oxford).
[12]
Superbases for Organic Synthesis: Guanidines, Amidines and Phosphazenes and Related Organocatalysts (Ed. T. Ishikawa) 2009 (Wiley-VCH: Weinheim).
[13]
(a) C.-J. Li, L. Chen, Chem. Soc. Rev. 2006, 35, 68. | CrossRef | (b) D. Dallinger, C. O. Kappe, Chem. Rev. 2007, 107, 2563. | CrossRef | (c) V. Polshettiwar, R. S. Varma, J. Org. Chem. 2007, 72, 7420. | CrossRef |
[14]
(a)
C. J. Li, T. H. Chan, Organic Reactions in Aqueous Media 1997 (John Wiley: New York, NY). (b)
Organic Synthesis in Water (Ed. P. A. Grieco) 1998 (Thomson Science: Glasgow) (c) U. M. Lindstrom, Chem. Rev. 2002, 102, 2751. | CrossRef | (d) C. J. Li, Chem. Rev. 2005, 105, 3095. | CrossRef | (e) C. J. Li, Chem. Rev. 1993, 93, 2023. | CrossRef | (f) A. Chanda, V. V. Fokin, Chem. Rev. 2009, 109, 725. | CrossRef | (g) R. N. Butler, A. G. Coyne, Chem. Rev. 2010, 110, 6302. | CrossRef |
[15]
K. Sugino, K. Shirai, R. Kitawaki, J. Org. Chem. 1961, 26, 4122. | CrossRef | CAS |
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