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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

Author(s): Mohammad Ali Nasseri *, Seyyedeh Ameneh Alavi, Milad Kazemnejadi and Ali Allahresani

Volume 17, Issue 11, 2020

Page: [857 - 863] Pages: 7

DOI: 10.2174/1570178616666190919110639

Price: $65

Abstract

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

Keywords: N-arylation, Manganese, Magnetic nanocatalyst, Mild conditions, N-arylimidazole, Chiral salen complex.

Graphical Abstract
[1]
Kurian, J.; Mathew, M.J. J. Magn. Magn. Mater., 2018, 451, 121-130.
[http://dx.doi.org/10.1016/j.jmmm.2017.10.124]
[2]
Huang, Y.Z.; Miao, H.; Zhang, Q.H.; Chen, C. Xu. J. Catal. Lett., 2008, 122, 344-348.
[http://dx.doi.org/10.1007/s10562-007-9386-0]
[3]
Nakhate, A.V.; Yadav, G.D. ChemistrySelect, 2017, 2, 2395-2405.
[http://dx.doi.org/10.1002/slct.201601846]
[4]
Henderson, A.S.; Medina, S.; Bower, J.F.; Galan, M.C. Org. Lett., 2015, 17(19), 4846-4849.
[http://dx.doi.org/10.1021/acs.orglett.5b02413] [PMID: 26379123]
[5]
Elhampour, A.; Nemati, F.; Kaveh, M. Chem. Lett., 2015, 45, 223-225.
[http://dx.doi.org/10.1246/cl.151097]
[6]
Teo, Y.C.; Yong, F.F.; Lim, G.S. Tetrahedron Lett., 2011, 52, 7171-7174.
[http://dx.doi.org/10.1016/j.tetlet.2011.10.128]
[7]
Lim, C.H.; Kudisch, M.; Liu, B.; Miyake, G.M. C-N Cross-Coupling via Photoexcitation of Nickel-Amine Complexes. J. Am. Chem. Soc., 2018, 140(24), 7667-7673.
[http://dx.doi.org/10.1021/jacs.8b03744] [PMID: 29787252]
[8]
Correa, A.; García Mancheño, O.; Bolm, C. Chem. Soc. Rev., 2008, 37(6), 1108-1117.
[http://dx.doi.org/10.1039/b801794h] [PMID: 18497924]
[9]
Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem. Int. Ed., 2007, 46, 934-936.
[10]
Kwon, M.A.; Kim, G. J. Catal. Today, 2003, 87, 145-151.
[http://dx.doi.org/10.1016/j.cattod.2003.09.008]
[11]
Zheng, W.; Tan, R.; Yin, S.; Zhang, Y.; Zhao, G.; Chen, Y.; Yin, D. Catal. Sci. Technol., 2015, 5, 2092-2102.
[http://dx.doi.org/10.1039/C4CY01290A]
[12]
Chakraborty, P.; Majumder, I.; Banu, K.S.; Ghosh, B.; Kara, H.; Zangrando, E.; Das, D. Dalton Trans., 2016, 45(2), 742-752.
[http://dx.doi.org/10.1039/C5DT03659C] [PMID: 26630495]
[13]
Gungor, E.; Kara, H. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2011, 82(1), 217-220.
[http://dx.doi.org/10.1016/j.saa.2011.07.038] [PMID: 21816668]
[14]
Balikesir, H.K. Z.; Naturforsch, B 2008, 63, 6-10.
[http://dx.doi.org/10.1515/znb-2008-0102]
[15]
Zidelmal, N.; Aubry-Barroca, N.; Lepoittevin, B.; Mellah, M.; Costa, L.; Ozanam, F.; Roger, P. Polymer (Guildf.), 2018, 135, 261-270.
[http://dx.doi.org/10.1016/j.polymer.2017.12.019]
[16]
An, Q.; Li, Z.; Graff, R.; Guo, J.; Gao, H.; Wang, C. ACS Appl. Mater. Interfaces, 2015, 7(8), 4969-4978.
[http://dx.doi.org/10.1021/acsami.5b00066] [PMID: 25674936]
[17]
Domínguez, I.; Fornés, V.; Sabater, M.J. J. Catal., 2004, 228, 92-99.
[http://dx.doi.org/10.1016/j.jcat.2004.08.021]
[18]
Islam, M.M.; Bhanja, P.; Halder, M.; Kundu, S.K.; Bhaumik, A.; Islam, S.M. RSC Advances, 2016, 6, 109315-109321.
[http://dx.doi.org/10.1039/C6RA21523H]
[19]
Yahsi, Y.; Kara, H. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2014, 127, 25-31.
[http://dx.doi.org/10.1016/j.saa.2014.02.060] [PMID: 24632152]
[20]
Yahsi, Y.; Gungor, E.; Coban, M.B.; Kara, H. Mol. Cryst. Liq. Cryst. (Phila. Pa.), 2016, 637, 67-75.
[http://dx.doi.org/10.1080/15421406.2016.1177918]
[21]
Yong, F.F.; Teo, Y.C. Synlett, 2012, 23, 2106-2110.
[http://dx.doi.org/10.1055/s-0032-1316682]
[22]
Teo, Y.C.; Yong, F.F.; Poh, C.Y.; Yan, Y.K.; Chua, G.L. Chem. Commun. (Camb.), 2009, (41), 6258-6260.
[http://dx.doi.org/10.1039/b909803h] [PMID: 19826687]
[23]
Kang, S.K.; Kim, J.S.; Choi, S.C. J. Org. Chem., 1997, 62(13), 4208-4209.
[http://dx.doi.org/10.1021/jo970656j] [PMID: 11671737]
[24]
Cahiez, G.; Razafintsalama, L.; Laboue, B.; Chau, F. Tetrahedron Lett., 1998, 39, 849-852.
[http://dx.doi.org/10.1016/S0040-4039(97)10747-X]
[25]
Sølvhøj, A.; Ahlburg, A.; Madsen, R. Chemistry, 2015, 21(45), 16272-16279.
[http://dx.doi.org/10.1002/chem.201502429] [PMID: 26377614]
[26]
Yong, F-F.; Teo, Y-C. Tetrahedron Lett., 2010, 51, 3910-3912.
[http://dx.doi.org/10.1016/j.tetlet.2010.05.098]
[27]
Dandia, A.; Jain, A.K.; Sharma, S. RSC Advances, 2013, 3(9), 2924-2934.
[http://dx.doi.org/10.1039/c2ra22477a]
[28]
Kumar, A.S.; Reddy, M.A.; Knorn, M.; Reiser, O.; Sreedhar, B. Eur. J. Org. Chem., 2013, 21, 4674-4680.
[http://dx.doi.org/10.1002/ejoc.201300343]
[29]
Sarode, S.A.; Bhojane, J.M.; Nagarkar, J.M. Tetrahedron Lett., 2015, 56, 206-210.
[http://dx.doi.org/10.1016/j.tetlet.2014.11.065]
[30]
Zou, X.; Wang, Y.; Wang, C.; Shi, K.; Ren, Y.; Zhao, X. Polymers (Basel), 2019, 11, 212.
[http://dx.doi.org/10.3390/polym11020212]
[31]
Kantam, M.L.; Roy, M.; Roy, S.; Sreedhar, B.; De, R.L. Catal. Commun., 2008, 9, 2226-2230.
[http://dx.doi.org/10.1016/j.catcom.2008.04.023]
[32]
Swami, S.; Agarwala, A.; Shrivastava, R. New J. Chem., 2016, 40(11), 9788-9794.
[http://dx.doi.org/10.1039/C6NJ02264B]

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