Abstract
Perovskite-type LaFeO3 nanoparticles were successfully prepared by a simple sol–gel method and used as a highly active, heterogeneous, and reusable nanocatalyst. The prepared catalyst was characterized by scanning electron microscopy, powder X-ray diffraction analysis, energy-dispersive X-ray spectroscopy, and Fourier-transform infrared (FT-IR) spectroscopy. The catalytic activity of LaFeO3 nanocatalyst was investigated in synthesis of β-amido ketone derivatives by reaction of acetophenone, different substituted aldehydes, nitriles, and acetyl chloride. This method offers several advantages such as environmental sustainability, low catalyst loading, easy workup and purification of products, excellent yield, and catalyst reusability of at least four times without any remarkable change in catalytic activity.
Graphical abstract
Perovskite-type LaFeO3 nanoparticles were prepared by a citric acid-based sol–gel route and successfully used as a heterogeneous and reusable nanocatalyst for convenient synthesis of β-amido ketones derivatives.
Similar content being viewed by others
References
F.K. Behbahani, N. Doragi, M.M. Heravi, Synth. Commun. 42, 5 (2012)
A.R. Momeni, M. Sadeghi, Appl. Catal. A 357, 1 (2009)
W.-C. Gao, F. Hu, Y.-M. Huo, H.-H. Chang, X. Li, W.-L. Wei, Org. Lett. 17, 15 (2015)
M. Mukhopadhyay, B. Bhatia, J. Iqbal, Tetrahedron Lett. 38, 6 (1997)
A.K. Tiwari, R.M. Kumbhare, S.B. Agawane, A.Z. Ali, K.V. Kumar, Bioorg. Med. Chem. Lett. 18, 14 (2008)
V. Shinu, B. Sheeja, E. Purushothaman, D. Bahulayan, Tetrahedron Lett. 50, 34 (2009)
T.A. Salama, S.S. Elmorsy, A.-G.M. Khalil, M.A. Ismail, Tetrahedron Lett. 48, 35 (2007)
X.-H. Zhang, J.-F. Yan, L. Fan, G.-B. Wang, D.-C. Yang, Acta. Pharm. Sin. B 1, 2 (2011)
M.R. Nabid, S.J.T. Rezaei, Appl. Catal. A 366, 1 (2009)
E. Rafiee, F. Shahbazi, M. Joshaghani, F. Tork, J. Mol. Catal. A: Chem. 242, 1 (2005)
Y. Wang, J. Zhou, K. Liu, L. Dai, J. Mol. Catal. A Chem. 366, 195 (2013)
M.A. Zolfigol, A. Khazaei, A. Zare, M. Mokhlesi, T. Hekmat-Zadeh, A. Hasaninejad, F. Derakhshan-Panah, A.R. Moosavi-Zare, H. Keypour, A.A. Dehghani-Firouzabadi, J. Chem. Sci. 124, 6 (2012)
R. Ghosh, S. Maiti, A. Chakraborty, S. Chakraborty, A.K. Mukherjee, Tetrahedron 62, 17 (2006)
A. Khazaei, M.A. Zolfigol, M. Mokhlesi, R. Rostamian, J. Iran. Chem. Soc. 10, 6 (2013)
M. Shokouhimehr, Catalysts 5, 2 (2015)
S. Shylesh, V. Schünemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 20 (2010)
S. Olveira, S.P. Forster, S. Seeger, J. Nanotech. 2014, 1 (2014)
S.B. Kalidindi, B.R. Jagirdar, ChemSusChem 5, 1 (2012)
S. Nakayama, J. Mater. Sci. 36, 23 (2001)
S.A. Mir, M. Ikram, K. Asokan, J. Phys: Conf. Ser. 534, 012017 (2014)
P.V. Serna, C.G. Campos, F.S. De Jesús, A.M.B. Miró, J. Lorán, J. Antonio, J. Longwell, J. Mater. Res. 19, 389 (2016)
M. O’Connell, A. Norman, C. Hüttermann, M. Morris, Catal. Today 47, 1 (1999)
F. Polo-Garzon, Z. Wu, J. Mater. Chem. A 6, 7 (2018)
S. Farhadi, F. Siadatnasab, J. Mol. Catal. A: Chem. 339, 1 (2011)
G. Shabbir, A. Qureshi, K. Saeed, Mater. Lett. 60, 29 (2006)
Y.-P. Luo, Q. Chen, Chem. Pap. 67, 5 (2013)
H. Mao, J. Wan, Y. Pan, Tetrahedron 65, 5 (2009)
D. Bahulayan, S.K. Das, J. Iqbal, J. Org. Chem. 68, 14 (2003)
L. Nagarapu, R. Bantu, R. Puttireddy, Appl. Catal. A 332, 2 (2007)
S. Ray, P. Das, B. Banerjee, A. Bhaumik, C. Mukhopadhyay, ChemPlusChem 80, 4 (2015)
G.S. Foo, F. Polo-Garzon, V. Fung, D.-E. Jiang, S.H. Overbury, Z. Wu, ACS Catal. 7, 7 (2017)
Acknowledgements
The authors are grateful to the University of Kashan for supporting this work by grant no. 159148/69.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Naeimi, H., Rahmatinejad, S. LaFeO3 perovskite nanoparticles as high-performance reusable catalyst for convenient synthesis of β-amido ketones under mild conditions. Res Chem Intermed 45, 3705–3721 (2019). https://doi.org/10.1007/s11164-019-03816-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-019-03816-1