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Letters in Organic Chemistry

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

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Research Article

Heck Cross-Coupling Reactions in Ionic Liquid mediated Pd Nanocatalysts

Author(s): Prashant Gautam and Vivek Srivastava*

Volume 18, Issue 5, 2021

Published on: 23 July, 2020

Page: [359 - 372] Pages: 14

DOI: 10.2174/1570178617999200723124636

Price: $65

Abstract

We straightforwardly synthesized 18 different types of palladium nanoparticles by using a series of palladium metal precursors and ionic liquids. All the materials went for XRD, TEM, and ICPOES analysis, before going to Heck cross-coupling reaction as a catalyst. We evaluated the catalytic performance of our developed IL#Pd MNP catalyst over Heck cross-coupling reaction between different terminal olefins with various 3-iodo-benzopyrones, including sterically hindered, electron-rich, electron neutral and electron-deficient systems. We obtained the Heck cross-coupling reaction product in good to average yield under phosphine free reaction condition with an added advantage of 6 times catalyst recycling.

Keywords: Ionic Liquid, palladium nanoparticles, Heck cross-coupling reaction, cross-coupling reaction, 3-iodo-benzopyrones.

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[1]
Kolahalam, L.A. Kasi Viswanath, I. V.; Diwakar, B.S.; Govindh, B.; Reddy, V.; Murthy, Y.L.N.Materials Today: Proceedings; Elsevier Ltd, 2019, Vol. 18, pp. 2182-2190.
[2]
Sharma, N.; Ojha, H.; Bharadwaj, A.; Pathak, D.P.; Sharma, R.K. RSC Advances, 2015, 5, 53381-53403.
[http://dx.doi.org/10.1039/C5RA06778B]
[3]
Trzeciak, A.M. Pd Nanoparticles for Coupling Reactions and Domino/Tandem Reactions.Nanocatalysis in Ionic Liquids; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2016, pp. 63-81.
[4]
Balanta, A.; Godard, C.; Claver, C. Chem. Soc. Rev., 2011, 40(10), 4973-4985.
[http://dx.doi.org/10.1039/c1cs15195a] [PMID: 21879073]
[5]
Chng, L.L.; Erathodiyil, N.; Ying, J.Y. Acc. Chem. Res., 2013, 46(8), 1825-1837.
[http://dx.doi.org/10.1021/ar300197s] [PMID: 23350747]
[6]
Khan, I.; Saeed, K.; Khan, I. Arab. J. Chem., 2017, 7, 908-931.
[7]
Fan, J.; Gao, Y. J. Exp. Nanosci., 2006, 1, 457-475.
[http://dx.doi.org/10.1080/17458080601067708]
[8]
Shenhar, R.; Norsten, T.B.; Rotello, V.M. Adv. Mater., 2005, 17, 657-669.
[http://dx.doi.org/10.1002/adma.200401291]
[9]
Boudjahem, A-G.; Redjel, A.; Mokrane, T. J. Ind. Eng. Chem., 2012, 18, 303-308.
[http://dx.doi.org/10.1016/j.jiec.2011.11.038]
[10]
Munnik, P.; de Jongh, P.E.; de Jong, K.P. Chem. Rev., 2015, 115(14), 6687-6718.
[http://dx.doi.org/10.1021/cr500486u] [PMID: 26088402]
[11]
Boudjahem, A-G.; Mokrane, T.; Redjel, A.; Bettahar, M.M. C. R. Chim., 2010, 13, 1433-1439.
[http://dx.doi.org/10.1016/j.crci.2010.06.022]
[12]
Lambert, S.; Cellier, C.; Grange, P.; Pirard, J-P.; Heinrichs, B. J. Catal., 2004, 221, 335-346.
[http://dx.doi.org/10.1016/j.jcat.2003.07.014]
[13]
Dhakshinamoorthy, A.; Navalon, S.; Alvaro, M.; Garcia, H. ChemSusChem, 2012, 5(1), 46-64.
[http://dx.doi.org/10.1002/cssc.201100517] [PMID: 22250135]
[14]
Polshettiwar, V.; Varma, R.S. Green Chem., 2010, 12, 743-754.
[http://dx.doi.org/10.1039/b921171c]
[15]
Migowski, P. Chemistry, 2007, 13, 32-39.
[http://dx.doi.org/10.1002/chem.200601438] [PMID: 17115465]
[16]
Kalidindi, S.B.; Jagirdar, B.R. ChemSusChem, 2012, 5(1), 65-75.
[http://dx.doi.org/10.1002/cssc.201100377] [PMID: 22190344]
[17]
Prechtl, M.H.G. Nanocatalysis in Ionic Liquids; wiley, 2016.
[18]
Olveira, S.; Forster, S.P.; Seeger, S. Nanocatalysis: Academic Discipline and Industrial Realities 2014.
[19]
Upadhyay, P.R.; Srivastava, V. Catal. Lett., 2017, 147, 1051-1060.
[http://dx.doi.org/10.1007/s10562-017-1995-7]
[20]
Scholten, J.D.; Leal, B.C.; Dupont, J. ACS Catal., 2012, 2, 184-200.
[http://dx.doi.org/10.1021/cs200525e]
[21]
Rocaboy, C.; Gladysz, J.A. New J. Chem., 2003, 27, 39-49.
[http://dx.doi.org/10.1039/b208545n]
[22]
Trzeciak, A.M.; Augustyniak, A.W. Coord. Chem. Rev., 2019, 384, 1-20.
[http://dx.doi.org/10.1016/j.ccr.2019.01.008]
[23]
Tao, R.; Miao, S.; Liu, Z.; Xie, Y.; Han, B.; An, G.; Ding, K. Green Chem., 2009, 11, 96-101.
[http://dx.doi.org/10.1039/B811587G]
[24]
Zhang, B.; Yan, N. Catalysts, 2013, 3, 543-562.
[http://dx.doi.org/10.3390/catal3020543]
[25]
Prechtl, M.H.G.; Scholten, J.D.; Dupont, J. Molecules, 2010, 15(5), 3441-3461.
[http://dx.doi.org/10.3390/molecules15053441] [PMID: 20657493]
[26]
Phan, N.T.S.; Van Der Sluys, M.; Jones, C.W. Adv. Synth. Catal., 2006, 348, 609-679.
[http://dx.doi.org/10.1002/adsc.200505473]
[27]
Pittelkow, M.; Moth-Poulsen, K.; Boas, U.; Christensen, J.B. Langmuir, 2003, 19, 7682-7684.
[http://dx.doi.org/10.1021/la0348822]
[28]
Panchal, M.; Kongor, A.; Mehta, V.; Vora, M.; Bhatt, K.; Jain, V. J. Saudi Chem. Soc., 2018, 22, 558-568.
[http://dx.doi.org/10.1016/j.jscs.2017.09.006]
[29]
Yang, Q.; Sane, N.; Klosowski, D.; Lee, M.; Rosenthal, T.; Wang, N.X.; Wiensch, E. Org. Process Res. Dev., 2019, 23, 2148-2156.
[http://dx.doi.org/10.1021/acs.oprd.9b00126]
[30]
Zim, D.; Nobre, S.M.; Monteiro, A.L. J. Mol. Catal. Chem., 2008, 287, 16-23.
[http://dx.doi.org/10.1016/j.molcata.2008.02.015]
[31]
Xu, L.; Chen, W.; Xiao, J. Organometallics, 2000, 19, 1123-1127.
[http://dx.doi.org/10.1021/om990956m]
[32]
Veerakumar, P.; Velayudham, M.; Lu, K.L.; Rajagopal, S. Appl. Catal. A Gen., 2013, 455, 247-260.
[http://dx.doi.org/10.1016/j.apcata.2013.01.021]
[33]
Umpierre, A.P.; Machado, G.; Fecher, G.H.; Morais, J. Dupont. J. Adv. Synth. Catal., 2005, 347, 1404-1412.
[http://dx.doi.org/10.1002/adsc.200404313]
[34]
Rafiee, E.; Joshaghani, M.; Abadi, P.G.S. J. Magn. Magn. Mater., 2016, 408, 107-115.
[http://dx.doi.org/10.1016/j.jmmm.2016.02.032]
[35]
Qiao, K.; Sugimura, R.; Bao, Q.; Tomida, D. Catal. Commun., 2008, 9, 2470-2474.
[http://dx.doi.org/10.1016/j.catcom.2008.06.016]
[36]
Movahed, S.K.; Dabiri, M.; Bazgir, A. Appl. Catal. A Gen., 2014, 488, 265-274.
[http://dx.doi.org/10.1016/j.apcata.2014.09.045]
[37]
Moreno-Mañas, M.; Pleixats, R. Acc. Chem. Res., 2003, 36(8), 638-643.
[http://dx.doi.org/10.1021/ar020267y] [PMID: 12924961]
[38]
Li, R.; Xu, H.; Zhao, N.; Jin, X.; Dang, Y. J. Org. Chem., 2020, 85, 301-305.
[http://dx.doi.org/10.1021/acs.joc.9b02489] [PMID: 31775003]
[39]
Liu, Y.; Wang, S-S.; Liu, W.; Wan, Q-X.; Wu, H-H.; Gao, G-H. Curr. Org. Chem., 2009, 13, 1322-1346.
[http://dx.doi.org/10.2174/138527209789055108]
[40]
Liu, G.; Hou, M.; Song, J.; Jiang, T.; Fan, H.; Zhang, Z.; Han, B. Green Chem., 2010, 12, 65-69.
[http://dx.doi.org/10.1039/B913182E]
[41]
Zhang, Y.; Lv, Z.; Zhong, H.; Zhang, M.; Zhang, T.; Zhang, W.; Li, K. Tetrahedron, 2012, 68, 9777-9787.
[http://dx.doi.org/10.1016/j.tet.2012.09.017]
[42]
Zhang, Y.; Lv, Z.; Zhang, M.; Li, K. Tetrahedron, 2013, 69, 8839-8846.
[http://dx.doi.org/10.1016/j.tet.2013.08.032]

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