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Letters in Organic Chemistry

Editor-in-Chief

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

Letter Article

Magnetically Recyclable Silica-Coated Magnetite-Molybdate Nanocatalyst and its Applications in N-Formylation Reactions Under Solvent-Free Conditions

Author(s): Runjhun Tandon, Shripad Patil*, Nitin Tandon* and Pushpendra Kumar

Volume 19, Issue 8, 2022

Published on: 12 January, 2022

Page: [616 - 626] Pages: 11

DOI: 10.2174/1570178619666220112112901

Price: $65

Abstract

A novel magnetite silica-coated nanoparticle-supported molybdate nanocatalyst has been prepared successfully by a simple co-precipitation method. Prepared nanocatalyst has been characterized by different techniques like Fourier Transmission Infrared Spectroscopy (FT-IR), X-ray diffraction (XRD), Field Emission Scanning Electron Microscope (FE-SEM), and Energy Dispersive X-ray Spectroscopy (EDX). Further, the catalytic activity of the nanocatalyst was explored for N-formylation reactions under solvent-free conditions. Interestingly, the catalyst could be reused for 10 cycles, and only 2 mol % of the catalyst was sufficient to catalyze the N-formylation reaction at 70°C under solvent-free conditions.

Keywords: Magnetic nanoparticles, N-formylation, catalytic activity, green chemistry, formamide derivatives, nanocatalyst.

Graphical Abstract

[1]
Chen, B-C.; Bednarz, M.S.; Zhao, R.; Sundeen, J.E.; Chen, P.; Shen, Z.; Skoumbourdis, A.P.; Barrish, J.C. Tet. Lett., 2000, 41(29), 5453-5456.
[http://dx.doi.org/10.1016/S0040-4039(00)00910-2]
[2]
Jackson, A.; Meth-Cohn, O. J. Chem. Soc. Chem. Commun., 1995, 13, 1319-1319.
[http://dx.doi.org/10.1039/c39950001319]
[3]
Kakehi, A.; Ito, S.; Hayashi, S.; Fujii, T. Bull. Chem. Soc. Jpn., 1995, 68(12), 3573-3580.
[http://dx.doi.org/10.1246/bcsj.68.3573]
[4]
Kobayashi, K.; Nagato, S.; Kawakita, M.; Morikawa, O.; Konishi, H. Chem. Lett., 1995, 24(7), 575-576.
[http://dx.doi.org/10.1246/cl.1995.575]
[5]
Lohray, B.B.; Baskaran, S.; Rao, B.S.; Reddy, B.Y.; Rao, I.N. Tet. Lett., 1999, 40(26), 4855-4856.
[http://dx.doi.org/10.1016/S0040-4039(99)00893-X]
[6]
Downie, I.M.; Earle, M.J.; Heaney, H.; Shuhaibar, K.F. Tetrahedron, 1993, 49(19), 4015-4034.
[http://dx.doi.org/10.1016/S0040-4020(01)89915-4]
[7]
Kobayashi, S.; Nishio, K. J. Org. Chem., 1994, 59(22), 6620-6628.
[http://dx.doi.org/10.1021/jo00101a021]
[8]
Kobayashi, S.; Yasuda, M.; Hachiya, I. Chem. Lett., 1996, 25(5), 407-408.
[http://dx.doi.org/10.1246/cl.1996.407]
[9]
Han, Y.; Cai, L. Tet. Lett., 1997, 38(31), 5423-5426.
[http://dx.doi.org/10.1016/S0040-4039(97)01206-9]
[10]
Martinez, J.; Laur, J. Synthesis, 1982, 11, 979-981.
[http://dx.doi.org/10.1055/s-1982-30034]
[11]
Bonin, M-A.; Giguere, D.; Roy, R. Tetrahedron, 2007, 63(23), 4912-4917.
[http://dx.doi.org/10.1016/j.tet.2007.03.152]
[12]
Gulevich, A.V.; Zhdanko, A.G.; Orru, R.V.; Nenajdenko, V.G. Chem. Rev., 2010, 110(9), 5235-5331.
[http://dx.doi.org/10.1021/cr900411f] [PMID: 20608735]
[13]
Jung, S-H.; Ahn, J-H.; Park, S-K.; Choi, J-K. Bull. Korean Chem. Soc., 2002, 23(1), 149-150.
[http://dx.doi.org/10.5012/bkcs.2002.23.1.149]
[14]
De Luca, L.; Giacomelli, G.; Porcheddu, A. Synlett, 2004, 14, 2570-2572.
[15]
Waki, M.; Meienhofer, J. J. Org. Chem., 1977, 42(11), 2019-2020.
[http://dx.doi.org/10.1021/jo00431a046] [PMID: 864543]
[16]
Reddy, P.G.; Kumar, G.K.; Baskaran, S. Tet. Lett., 2000, 41(47), 9149-9151.
[http://dx.doi.org/10.1016/S0040-4039(00)01636-1]
[17]
Deutsch, J.; Eckelt, R.; Köckritz, A.; Martin, A. Tetrahedron, 2009, 65(50), 10365-10369.
[http://dx.doi.org/10.1016/j.tet.2009.10.047]
[18]
Patre, R.E.; Mal, S.; Nilkanth, P.R.; Ghorai, S.K.; Deshpande, S.H.; El Qacemi, M.; Smejkal, T.; Pal, S.; Manjunath, B.N. Chem. Commun. (Camb.), 2017, 53(15), 2382-2385.
[http://dx.doi.org/10.1039/C6CC07679C] [PMID: 28174765]
[19]
Deutsch, J.; Niclas, H-J. Synth. Commun., 1993, 23(11), 1561-1568.
[http://dx.doi.org/10.1080/00397919308011251]
[20]
Kisfaludy, L.; Otvos, L., Jr Synthesis (Stuttgart), 1987, 5, 510.
[http://dx.doi.org/10.1055/s-1987-27987]
[21]
Hill, D.R.; Hsiao, C-N.; Kurukulasuriya, R.; Wittenberger, S.J. Org. Lett., 2002, 4(1), 111-113.
[http://dx.doi.org/10.1021/ol016976d] [PMID: 11772103]
[22]
Hosseini-Sarvari, M.; Sharghi, H. J. Org. Chem., 2006, 71(17), 6652-6654.
[http://dx.doi.org/10.1021/jo060847z] [PMID: 16901164]
[23]
Kim, J-G.; Jang, D-O. Bull. Korean Chem. Soc., 2010, 31(10), 2989-2991.
[http://dx.doi.org/10.5012/bkcs.2010.31.10.2989]
[24]
Shekhar, A.C.; Kumar, A.R.; Sathaiah, G.; Paul, V.L.; Sridhar, M.; Rao, P.S. Tet. Lett., 2009, 50(50), 7099-7101.
[http://dx.doi.org/10.1016/j.tetlet.2009.10.006]
[25]
Yadav, L.R.; Raghavendra, M.; Kumar, K.S.; Dhananjaya, N.; Nagaraju, G. Eur. Phys. J. Plus, 2018, 133(4), 153.
[http://dx.doi.org/10.1140/epjp/i2018-11963-6]
[26]
Yadav, L.R.; Raghavendra, M.; Manjunath, K.; Nagaraju, G. J. Mater. Sci. Mater. Electron., 2018, 29(10), 8747-8759.
[http://dx.doi.org/10.1007/s10854-018-8891-9]
[27]
Kim, J-G.; Jang, D.O. Synlett, 2010, 08, 1231-1234.
[28]
Kim, J-G.; Jang, D.O. Synlett, 2010, 14, 2093-2096.
[29]
Hu, Q-L.; Wang, L-S.; Yu, N-N.; Zhang, Z-F.; Zheng, X.; Hu, X-M. Rare Met., 2020, 39(8), 1333-1340.
[http://dx.doi.org/10.1007/s12598-017-0940-7]
[30]
Qu, J.; Che, T.; Shi, L.; Lu, Q.; Qi, S. Chin. Chem. Lett., 2019, 30(6), 1198-1203.
[http://dx.doi.org/10.1016/j.cclet.2019.01.021]
[31]
Chen, J.; Lu, Z-H.; Wang, Y.; Chen, X.; Zhang, L. Int. J. Hydrogen Energy, 2015, 40(14), 4777-4785.
[http://dx.doi.org/10.1016/j.ijhydene.2015.02.054]
[32]
Chen, M-N.; Mo, L-P.; Cui, Z-S.; Zhang, Z-H. Chemistry, 2019, 15, 27-37.
[33]
Zhang, M.; Liu, Y-H.; Shang, Z-R.; Hu, H-C.; Zhang, Z-H. Catal. Commun., 2017, 88, 39-44.
[http://dx.doi.org/10.1016/j.catcom.2016.09.028]
[34]
Ma’mani, L.; Sheykhan, M.; Heydari, A.; Faraji, M.; Yamini, Y. Appl. Catal. A Gen., 2010, 377(1-2), 64-69.
[http://dx.doi.org/10.1016/j.apcata.2010.01.020]
[35]
Khojastehnezhad, A.; Rahimizadeh, M.; Moeinpour, F.; Eshghi, H.; Bakavoli, M. C. R. Chim., 2014, 17(5), 459-464.
[http://dx.doi.org/10.1016/j.crci.2013.07.013]
[36]
Kooti, M.; Nasiri, E. Chemical, 2015, 406, 168-177.
[http://dx.doi.org/10.1016/j.molcata.2015.05.009]
[37]
Habibi, D.; Heydari, S.; Afsharfarnia, M. Appl. Organomet. Chem., 2017, 31(12), e3874.
[http://dx.doi.org/10.1002/aoc.3874]
[38]
Do Kim, K.; Kim, S.S.; Choa, Y-H.; Kim, H.T. J. Ind. Eng. Chem., 2007, 13(7), 1137-1141.
[39]
Chen, Y.; Peng, Z.; Kong, L.X.; Huang, M.F.; Li, P.W. Polym. Eng. Sci., 2008, 48(9), 1674-1677.
[http://dx.doi.org/10.1002/pen.20997]
[40]
Dewanto, A. IOP Conference Series: Materials Science and Engineering; IOP Publishing, 2018, p. 012010.
[41]
Shao, H.; Qi, J.; Lin, T.; Zhou, Y. Ceram. Int., 2018, 44(2), 2255-2260.
[http://dx.doi.org/10.1016/j.ceramint.2017.10.184]
[42]
Arandiyan, H.R.; Parvari, M. J. Nat. Gas Chem., 2008, 17, 213-224.
[http://dx.doi.org/10.1016/S1003-9953(08)60054-7]
[43]
Masoudian, S.K.; Sadighi, S.; Tofigh, A.; Kho-dadadi, Z. J. Appl. Res. Chem., 2014, 7(4), 39-45.
[44]
Chithambararaj, A.; Mathi, D.B.; Yogamalar, N.R.; Bose, A.C. Mater. Res. Express, 2015, 2(5), 055004.
[http://dx.doi.org/10.1088/2053-1591/2/5/055004]
[45]
Kee, C.W. J. Chem., 2015, 439270.
[http://dx.doi.org/10.1155/2015/439270]
[46]
Sharma, V.; Kuma, P.; Shrivastava, J.; Solanki, A.; Satsangi, V.R.; Dass, S.; Shrivastav, R. Int. J. Hydrogen Energy, 2011, 36, 4280-4290.
[http://dx.doi.org/10.1016/j.ijhydene.2011.01.004]
[47]
Yadav, J.K.; Yadav, P.; Awasthi, S.K.; Agarwal, A. RSC Advances, 2020, 10, 41229-41236.
[http://dx.doi.org/10.1039/D0RA07476D]
[48]
King, B.H.; Wang, M.L.; Jesse, K.A.; Kaur, G.; Tran, B.; Walser-Kuntz, R.; Iafe, R.G.; Wenzel, A.G. J. Org. Chem., 2020, 85(20), 13256-13263.
[http://dx.doi.org/10.1021/acs.joc.0c01552] [PMID: 32975945]
[49]
Gerack, C.J.; McElwee-White, L. Molecules, 2014, 19(6), 7689-7713.
[http://dx.doi.org/10.3390/molecules19067689] [PMID: 24918541]
[50]
Desai, B.; Danks, T.N.; Wagner, G. Lett, 2005, 46, 955-957.
[51]
Sonawane, R.B.; Rasal, N.K.; Jagtap, S.V. Org. Lett., 2017, 19(8), 2078-2081.
[http://dx.doi.org/10.1021/acs.orglett.7b00660] [PMID: 28375017]
[52]
Habibi, D.; Rahmani, P.A. J. Chem., 2013, 10, 1155.
[http://dx.doi.org/10.1155/2013/972960]
[53]
Khatri, C.K.; Chaturbhuj, G.U.J. Iran. Chem. Soc, 2017, 14(12), 1186.
[http://dx.doi.org/10.1007/s13738-017-1186-x]
[54]
Lei, M.; Ma, L.; Hu, L.A. Tet. Lett., 2010, 51, 4186-4188.
[http://dx.doi.org/10.1016/j.tetlet.2010.06.005]
[55]
Hosseini-Sarvari, M.; Safary, E.; Jarrahpour, A.; Heiran, R. C. R. Chim., 2012, 15, 980.
[http://dx.doi.org/10.1016/j.crci.2012.09.014]
[56]
Krishnakumar, B.; Swaminathan, M.A. J. Mol. Catal. Chem., 2011, 334, 98.
[http://dx.doi.org/10.1016/j.molcata.2010.11.002]
[57]
Yang, X.J.; Zhang, Y.S. Intermed., 2013, 39, 2833.
[58]
Seddighi, M.; Shirini, F.; Mamaghani, M. Iran. Chem. Soc, 2015, 12, 433.
[http://dx.doi.org/10.1007/s13738-014-0500-0]
[59]
Chen, Z.; Fu, R.; Chai, W.; Zheng, H.; Sun, L.; Lu, Q.; Yuan, R. Tetrahedron, 2014, 70(13), 2237-2245.
[http://dx.doi.org/10.1016/j.tet.2014.02.042]
[60]
Pace, V.; de la Vega-Hernández, K.; Urban, E.; Langer, T. Org. Lett., 2016, 18(11), 2750-2753.
[http://dx.doi.org/10.1021/acs.orglett.6b01226] [PMID: 27218199]
[61]
Yu, S.; Song, K.H.; Lee, S. Asian J. Org. Chem., 2019, 8(9), 1613-1616.
[http://dx.doi.org/10.1002/ajoc.201900216]
[62]
Jia, M.; Zhang, H.; Lin, Y.; Chen, D.; Chen, Y.; Xia, Y. Org. Biomol. Chem., 2018, 16(19), 3615-3624.
[http://dx.doi.org/10.1039/C8OB00490K] [PMID: 29708257]
[63]
Majumdar, S.; De, J.; Hossain, J.; Basak, A. Tet. Lett., 2013, 54(3), 262-266.
[http://dx.doi.org/10.1016/j.tetlet.2012.11.017]
[64]
Kao, H-M.; Ting, C-C.; Chiang, A.S.; Teng, C-C.; Chen, C-H. Chem. Commun. (Camb.), 2005, 8(8), 1058-1060.
[http://dx.doi.org/10.1039/b414786c] [PMID: 15719115]
[65]
Dine, T.M.E.; Evans, D.; Rouden, J. Blanchet. J. Chem., 2016, 22(17), 5894-5898.
[http://dx.doi.org/10.1002/chem.201600234] [PMID: 26946179]

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