Claisen–Schmidt Condensation Catalyzed by Metal-Organic Frameworks
mass balances of the recovered reaction mixture accounted
for more than 90% of the initial substrate as confirmed by
GC using nitrobenzene as external standard. The products
were analyzed by GC and characterized by GC-MS. The
yield of the chalcone was determined by mmol of aldehyde
and mmol of ketone converted in a given time to form the
corresponding chalcone.
A similar procedure was followed for the synthesis of
chalcone with other catalysts (iron citrate and FeCl3·6H2O)
in the presence of toluene as solvent maintaining the same
[10] K. Wilson, A. F. Lee, D. J. Macquarrie, J. H. Clark,
Appl. Catal. A: Gen. 2002, 228, 127.
[11] J. Shen, H. Wang, H. Liu, Y. Sun, Z. Liu, J. Mol. Catal.
A: Chem. 2008, 280, 24.
[12] L. B. Kunde, S. M. Gade, V. S. Kalyani, S. P. Gupte,
Catal. Commun. 2009, 10, 1881.
[13] A. Guida, M. H. Lhouty, D. Tichit, F. Figueras, P. Gen-
este, Appl. Catal. A: Gen. 1997, 164, 251.
[14] M. Lakshmi Kantam, B. Veda Prakash, Ch. Venkat
Reddy, Synth. Commun. 2005, 35, 1971.
iron content as for the Fe
G
[15] P. Formentin, H. Garcia, A. Leyva, J. Mol. Catal. A
2004, 214, 137.
[16] M. J. Climent, H. Garcia, J. Primo, Catal. Lett. 1990, 4,
85.
[17] R. Srivastava, N. Iwasa, S.-I. Fujita, M. Arai, Chem.
Eur. J. 2008, 14, 9507.
Experimental Procedure for Reusability Tests
The reusability of FeACHTNUGRTENUNG(BTC) was tested for the synthesis of
chalcone. At the end of the reaction, the mixture was fil-
tered and the catalyst was washed with fresh toluene and
dried at 708C for 2 h, then reused without further purifica-
tion for a second run with fresh benzaldehyde and acetophe-
[18] M. J. Climent, A. Corma, S. Iborra, J. Primo, J. Catal.
1995, 151, 60.
[19] R. Sheldon, I. Arends, U. Hanefeld, Green Chemistry
and Catalysis, Wiley-VCH, Weinheim, 2007.
[20] A. Corma, J. Catal. 2003, 216, 298.
none. After the second use, the resulting FeACTHNURTGNEU(GN BTC) was used
for a third consecutive run wherein a minor loss in activity
was observed. Crystallinity of the three-times used sample
was compared by powder XRD.
[21] J. Y. Lee, O. K. Farha, J. Roberts, K. A. Scheidt, S. T.
Nguyen, J. T. Hupp, Chem. Soc. Rev. 2009, 38, 1450.
[22] S. L. James, Chem. Soc. Rev. 2003, 32, 276.
[23] Z. Wang, G. Chen, K. Ding, Chem. Rev. 2009, 109, 322.
[24] D. Farrusseng, S. Aguado, C. Pinel, Angew. Chem.
2009, 121, 7638; Angew. Chem. Int. Ed. 2009, 48, 7502.
[25] A. Dhakshinamoorthy, M. Alvaro, H. Garcia, J. Catal.
2009, 267, 1.
Acknowledgements
Financial support by the Spanish DGI (CTQ06-6857 and
CTQ2007-67805/PPQ) and European Commission (MACA-
DEMIA) is gratefully acknowledged.
[26] A. Dhakshinamoorthy, M. Alvaro, H. Garcia, Adv.
Synth. Catal. 2009, 351, 2271,.
[27] L. Alaerts, E. Seguin, H. Poelman, F. Thibault-Starzyk,
P. A. Jacobs, D. E. De Vos, Chem. Eur. J. 2006, 12,
7353.
[28] P. Horcajada, S. Surble, C. Serre, D.-Y. Hong, Y.-K.
Seo, J.-S. Chang, J.-M. Greneche, I. Margiolaki, G.
Ferey, Chem. Commun. 2007, 2820.
References
[1] D. N. Dhar, The Chemistry of Chalcones and Related
Compounds, Wiley, New York, 1981.
[29] G. Ferey, C. Mellot-Draznieks, C. Serre, F. Millange, J.
Dutour, S. Surble, I. Margiolaki, Science 2005, 309,
2040.
[30] T. Loiseau, C. Serre, C. Huguenard, G. Fink, F. Tau-
lelle, M. Henry, T. Bataille, G. Ferey, Chem. Eur. J.
2004, 10, 1373.
[2] Y. Xia, Z. Y. Yang, K. F. Bastow, Y. Nakanishi, K. H.
Lee, Bioorg. Med. Chem. Lett. 2000, 10, 699.
[3] H. K. Hsieh, L. T. Tsao, J. P. Wang, J. Pharm. Pharma-
col. 2000, 52, 163.
[4] J. Rojas, M. Paya, J. N. Dominguez, M. L. Ferrandiz,
Bioorg. Med. Chem. Lett. 2002, 12, 1951.
[31] I. A. Baburin, S. Leoni, G. Seifert, J. Phys. Chem. B
[5] M. Satyanarayana, P. Tiwari, B. K. Tripathi, A. K. Sri-
vastava, R. Pratap, Bioorg. Med. Chem. 2004, 12, 883.
[6] P. W. N. M. van Leeuwen, Homogeneous Catalysis-Un-
derstanding the Art, Kluwer Academic Publishers: Dor-
drecht, 2004.
2008, 112, 9437.
A minimal formal correction has been carried out since the
first online publication of this article. In Table 2, entry 8, the
yield has been corrected to 6 (54) from 31 (54) in the first
online publication.
[7] A. Corma, H. Garcia, Chem. Rev. 2003, 103, 4307.
[8] F. Dong, C. Jian, F. Zhenghao, G. Kai, L. Zuliang,
Catal. Commun. 2008, 9, 1924.
[9] Q. Xu, Z. Yang, D. Yin , F. Zhang, Catal. Commun.
2008, 9, 1579.
Adv. Synth. Catal. 2010, 352, 711 – 717
ꢂ 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
717