Abstract
A new multifunctional bimetallic nanocatalyst was prepared by immobilization of Cu/Ni-doped sulfated zirconium oxide on magnetic cadmium ferrite (CdFe2O4@SiO2@ZrO2/SO42−/Cu/Ni) and used as an efficient recyclable catalyst for one-pot as well as stepwise preparation of α-aminonitriles under mild conditions. The magnetic nanocatalyst was characterized by FTIR, TGA, VSM, XRD, EDX, FE-SEM, and TEM analyses. Also, the surface acidity of the catalyst was measured by pyridine adsorption assay. The catalyst possesses various active sites which could catalyst a variety of aromatic and aliphatic aldehydes to the corresponding α-amionitriles under moderate to high yields in the presence of aniline. Furthermore, transformation of ketones to the desired α-amionitriles and some bis-aminonitriles was also performed by this method. The catalyst could be readily recovered from the reaction mixture and reused for several times without significant loss of activity.
Graphic abstract
A general and efficient method has been developed for transformation of a variety of aliphatic, aromatic aldehydes and ketones to the corresponding α-aminonitriles using a multifunctional recyclable CdFe2O4@SiO2@ZrO2/SO42−/Cu/Ni nanocatalyst.
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References
P. Wu, L. Feng, Y. Liang, X. Zhang, B. Mahmoudi, M. Kazemnejadi, Appl. Catal. A Gen. 590, 117301 (2020)
M. Kazemnejadi, S.A. Alavi, Z. Rezazadeh, M.A. Nasseri, A. Allahresani, M. Esmaeilpour, Appl. Organomet. Chem. 34, e5388 (2019)
E. Eidi, M.Z. Kassaee, Z. Nasresfahani, P.T. Cummings, Res. Chem. Intermed. 45, 303 (2019)
E. Ezzatzadeh, Z. Hossaini, Nat. Prod. Res. 33, 1 (2018)
A. Maleki, E. Akhlaghi, R. Paydar, Appl. Organomet. Chem. 30, 382 (2016)
V.V. Kouznetsov, C.E.P. Galvis, Tetrahedron 74, 773 (2018)
C. Bolm, J.G. Hernández, Chemsuschem 11, 1410 (2018)
J.Q. Liu, A. Shatskiy, B.S. Matsuura, M.D. Kärkäs, Synthesis 51, 2759 (2019)
H. Inada, M. Shibuya, Y. Yamamoto, Org. Lett. 21, 709 (2019)
J.W. Lown, A.V. Joshua, J.S. Lee, Biochemistry 21, 419 (1982)
B. Ahrén, Best Pract. Res. Clin. Endocrinol. Metab. 23, 487 (2009)
R. Krishnamurthy, V. Snieckus, Synlett 28, 27 (2017)
E.J. Corey, D.Y. Gin, R.S. Kania, J. Am. Chem. Soc. 118, 9202 (1996)
S.A. Benner, H.J. Kim, M.J. Kim, A. Ricardo, Cold Spring Harbor Perspect. Boil. 2, a003467 (2010)
A. Bahrani, Z. Karimi-Jaberi, Monatsh. Chem. 150, 303 (2019)
M.G. Dekamin, Z. Mokhtari, Tetrahedron 68, 922 (2012)
M. Shekouhy, Catal. Sci. Technol. 2, 1010 (2012)
G.A. Olah, T. Mathew, C. Panja, K. Smith, G.K.S. Prakash, Catal. Lett. 114, 1 (2007)
E. Rafiee, A. Azad, M. Joshaghani, Lett. Org. Chem. 4, 60 (2007)
C. Li, M. Iqbal, J. Lin, X. Luo, B. Jiang, V. Malgras, K.C.W. Wu, J. Kim, Y. Yamauchi, Acc. Chem. Res. 51, 1764 (2018)
C. Li, H. Tan, J. Lin, X. Luo, S. Wang, J. You, Y.M. Kang, Y. Bando, Y. Yamauchi, J. Kim, Nano Today 21, 105 (2018)
M.A. Nasseri, M. Kazemnejadi, B. Mahmoudi, F. Assadzadeh, S.A. Alavi, A. Allahresani, J. Nanopart. Res. 21, 214 (2019)
M.A. Nasseri, S.A. Alavi, M. Kazemnejadi, A. Allahresani, ChemistrySelect 4, 8493 (2019)
M.A. Nasseri, S.A. Alavi, M. Kazemnejadi, A. Allahresani, RSC Adv. 9, 20749 (2019)
X. Li, K. Nagaoka, L.J. Simon, R. Olindo, J.A. Lercher, A. Hofmann, J. Sauer, J. Am. Chem. Soc. 127, 16159 (2005)
A. Galadima, R.P.K. Wells, J.A. Anderson, Appl. Petrochem. Res. 1, 35 (2012)
O. Afzal, S. Kumar, M.R. Haider, M.R. Ali, R. Kumar, M. Jaggi, S. Bawa, Eur. J. Med. Chem. 97, 871 (2015)
R.F. Perez, S.J. Canhaci, L.E. Borges, M.A. Fraga, Catal. Today 289, 273 (2017)
M.K. Mishra, B. Tyagi, R.V. Jasra, J. Mol. Catal. A: Chem. 223, 61 (2004)
F. Heshmatpour, R.B. Aghakhanpour, Adv. Powder Technol. 23, 80 (2012)
D. Sarkar, D. Mohapatra, S. Ray, S. Bhattacharyya, S. Adak, N. Mitra, Ceram. Int. 33, 1275 (2007)
G. Shi, F. Yu, Y. Wang, D. Pan, H. Wang, R. Li, Renewable Energy 92, 22 (2016)
D.P. Volanti, D. Keyson, L.S. Cavalcante, A.Z. Simões, M.R. Joya, E. Longo, J.A. Varela, P.S. Pizani, A.G. Souza, J. Alloys Compd. 459, 537 (2008)
A. Othonos, M. Zervos, Nanoscale Res. Lett. 6, 622 (2011)
A. Rahdar, M. Aliahmad, Y. Azizi, J. Nanostruct. 5, 145 (2015)
K. Kalpanadevi, C.R. Sinduja, R. Manimekalai, Int. J. Nanosci. 16, 1750002 (2017)
P.K. Nayak, Mater. Chem. Phys. 112, 24 (2008)
W. Shi, X. Liu, T. Zhang, Q. Wang, L. Zhang, RSC Adv. 5, 51027 (2015)
M. Kazemnejadi, S.A. Alavi, Z. Rezazadeh, M.A. Nasseri, A. Allahresani, M. Esmaeilpour, Green Chem. 21, 1718 (2019)
A.K. Aboul-Gheit, F.K. Gad, G.M. Abdel-Aleem, D.S. El-Desouki, S.M. Abdel-Hamid, S.A. Ghoneim, A.H. Ibrahim, Egypt. J. Pet. 23, 303 (2014)
J. Datka, A.M. Turek, J.M. Jehng, I.E. Wachs, J. Catal. 135, 186 (1992)
P. Li, Y. Zhang, Z. Chen, X. Zhang, Tetrahedron Lett. 58, 1854 (2017)
M. Kazemnejadi, A.R. Sardarian, RSC Adv. 6, 91999 (2016)
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Nasseri, M.A., Ramezani-Moghadam, S., Kazemnejadi, M. et al. Cu/Ni-doped sulfated zirconium oxide immobilized on CdFe2O4 NPs: a cheap, sustainable and magnetically recyclable inorgano-catalyst for the efficient preparation of α-aminonitriles in aqueous media. Res Chem Intermed 46, 4233–4256 (2020). https://doi.org/10.1007/s11164-020-04203-x
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DOI: https://doi.org/10.1007/s11164-020-04203-x