Green Synthesis of Pd Nanoparticles Mediated by Thymbra Spicata Leaves Extract and Its Application as a Recyclable Nanocatalyst for Reduction of 4-Nitrophenol and Suzuki Reactions
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Abstract
A simple and ecological pathway for the procurement of palladium nanoparticles (Pd NPs) was developed, applying the non-toxic and sustainable natural extract from Thymbra spicata leaves as the reducing, stabilizing and capping agent. UV–vis spectroscopy, X-ray diffraction, Fourier transformed infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy and energy dispersive X-ray spectroscopy, were utilized to classify the synthesized Pd NPs@Thymbra spicata catalyst. The Pd NPs@Thymbra spicata demonstrated excellent behavior as a reusable nanocatalyst in Suzuki–Miyaura cross-coupling reactions and reduction of 4-nitrophenol at room temperature. The nanocatalyst was reused in numerous runs with excellent product yields and without any significant deduction in catalytic behavior.
Graphical Abstract
Keywords
Pd nanoparticles Thymbra spicata Green chemistry 4-Nitrophenol SuzukiNotes
Acknowledgements
We are thankful to Department of Pharmaceutical Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran, for partial support of this work.
References
- 1.S. Iravani, Green Chem. 13, 2638 (2011)CrossRefGoogle Scholar
- 2.H. Zhu, M.L. Du, M. Zou, C. Xu, Y.Q. Fu, Dalton Trans. 41, 10465 (2012)CrossRefGoogle Scholar
- 3.P. Raveendran, J. Fu, S.L. Wallen, J. Am. Chem. Soc. 125, 13940 (2003)CrossRefGoogle Scholar
- 4.S.B. Kalidindi, B.R. Jagirdar, ChemSusChem 5, 65 (2012)CrossRefGoogle Scholar
- 5.R.S. Varma, Curr. Opin. Chem. Eng 1, 123 (2012)CrossRefGoogle Scholar
- 6.B. Nakhjavan, M.N. Tahir, F. Natalio, H. Gao, K. Schneider, T. Schladt, I. Ament, R. Branscheid, S. Weber, U. Kolb, C. Sönnichsen, L.M. Schreiber, W. Tremel, J. Mater. Chem 21, 8605 (2011)CrossRefGoogle Scholar
- 7.M.N. Tahir, F. Natalio, M.A. Cambaz, M. Panthöfer, R. Branscheid, U. Kolb, W. Tremel, Nanoscale 5, 9944 (2013)CrossRefGoogle Scholar
- 8.J.R. Peralta-Videa, L. Zhao, M.L. Lopez-Moreno, G. Rosa, J. Hong, J.L. Gardea-Torresdey, J. Hazard. Mater. 186, 1 (2011)CrossRefGoogle Scholar
- 9.K. Byrappa, S. Ohara, T. Adschiri, Adv. Drug Deliv. Rev. 60, 299 (2008)CrossRefGoogle Scholar
- 10.J.M. Campelo, D. Luna, R. Luque, J.M. Marinas, A.A. Romero, ChemSusChem. 2, 18 (2009)CrossRefGoogle Scholar
- 11.S.V. Otari, R.M. Patil, S.R. Waghmare, J. Ghosha, SH. Pawar, Dalton Trans. 42, 9966 (2013)CrossRefGoogle Scholar
- 12.T. Hennebel, S.D. Corte, W. Verstraete, N. Boon, Curr. Opin. Biotechnol. 23, 555 (2012)CrossRefGoogle Scholar
- 13.M.N. Tahir, F. Natalio, H.A. Therese, A. Yella, N. Mets, M.R. Shah, E. Mugnaioli, R. Berger, P. Theato, H.C. Schroeder, W.E.G. Mueller, W. Tremel, Adv. Funct. Mater. 19, 285 (2009)CrossRefGoogle Scholar
- 14.M.N. Tahir, P. Théato, W.E.G. Müller, H.C. Schröder, A. Boreijko, S. Faiß, A. Janshoff, J. Huth, W. Tremel, Chem. Commun. 44 5533 (2005)CrossRefGoogle Scholar
- 15.M.S. Akhtar, J. Panwar, Y.S. Yun, ACS Sustain. Chem. Eng 1, 591 (2013)CrossRefGoogle Scholar
- 16.A.K. Mittal, Y. Chisti, U.C. Banerjee, Biotechnol. Adv. 31, 346 (2013)CrossRefGoogle Scholar
- 17.H. Veisi, S. Hemmati, H. Shirvani, H. Veisi, Appl. Organomet. Chem. 30, 387 (2016)CrossRefGoogle Scholar
- 18.P.P. Gan, S.F.Y. Li, Rev. Environ. Sci. Biotechnol. 11, 169 (2012)CrossRefGoogle Scholar
- 19.F. Coccia, L. Tonucci, D. Bosco, M. Bressan, N. d’Alessandro, Green Chem. 14, 1073 (2012)CrossRefGoogle Scholar
- 20.F. Cheng, J.W. Betts, S.M. Kelly, J. Schaller, T. Heinze, Green Chem. 15, 989 (2013)CrossRefGoogle Scholar
- 21.K.M. Kumar, B.K. Mandal, S.K. Tammina, RSC Adv. 3, 4033 (2013)CrossRefGoogle Scholar
- 22.G. Zhang, M. Du, Q. Li, X. Li, J. Huang, X. Jiang, D. Sun, RSC Adv. 3, 1878 (2013)CrossRefGoogle Scholar
- 23.H.J. Lee, J.Y. Song, B.S. Kim, J. Chem. Technol. Biotechnol. 88, 1971 (2013)Google Scholar
- 24.P. Dauthal, M. Mukhopadhyay, Ind. Eng. Chem. Res. 51, 13014 (2012)CrossRefGoogle Scholar
- 25.Z. Shen, G. Han, X. Wang, J. Luo, R. Sun, J. Mater. Chem. B 5, 1155 (2017)CrossRefGoogle Scholar
- 26.G. Han, X. Li, J. Li, X. Wang, Y.S. Zhang, R. Sun, ACS Omega 2, 4938 (2017)CrossRefGoogle Scholar
- 27.Z. Shen, G. Han, C. Liu, X. Wang, R. Sun, J. Alloys Compd. 686, 82 (2016)CrossRefGoogle Scholar
- 28.K.D. Arunachalam, S.K. Annamalai, S. Hari, Int. J. Nanomed. 8, 1307 (2013)CrossRefGoogle Scholar
- 29.F. Zaera, Chem. Soc. Rev. 42, 2746 (2013)CrossRefGoogle Scholar
- 30.G.C. Fortman, S.P. Nolan, Chem. Soc. Rev. 40, 5151 (2011)CrossRefGoogle Scholar
- 31.A.J. Hickman, M.S. Sanford, Nature 484, 177 (2012)CrossRefGoogle Scholar
- 32.R. Ghorbani-Vaghei, S. Hemmati, M. Hashemi, H. Veisi, C. R. Chimie 18, 636 (2015)CrossRefGoogle Scholar
- 33.M. Pirhayati, H. Veisi, A. Kakanejadifard, RSC Adv. 6, 27252 (2016)CrossRefGoogle Scholar
- 34.B. Abbas Khakiani, K. Pourshamsian, H. Veisi, Appl. Organomet. Chem. 29, 259 (2015)CrossRefGoogle Scholar
- 35.M. Zhu, Y. Wang, C. Wang, W. Li, G. Diao, Catal. Sci. Technol. 3, 952 (2013)CrossRefGoogle Scholar
- 36.Y. Lu, H. Zhu, W. Li, B. Hu, S. Yu, J. Mater. Chem. A 1, 3783 (2013)CrossRefGoogle Scholar
- 37.S. Santra, P. Ranjan, P. Bera, P. Ghosh, S. K. Mandal, RSC Adv. 2, 7523 (2012)CrossRefGoogle Scholar
- 38.S. Deng, J. Lei, Y. Huang, X. Yao, L. Ding, H. Ju, Chem. Commun. 48, 9159 (2012)CrossRefGoogle Scholar
- 39.H. Itoh, H. Maeda, S. Yamada, Y. Hori, ChemCatChem 4, 1737 (2012)CrossRefGoogle Scholar
- 40.S. Cacchi, E. Caponetti, M.A. Casadei, A.D. Giulio, G. Fabrizi, G. Forte, A. Goggiamani, S. Moreno, P. Paolicelli, F. Petrucci, A. Prastaro, M.L. Saladino, Green Chem. 14, 317 (2012)CrossRefGoogle Scholar
- 41.H. Veisi, R. Masti, D. Kordestani, M. Safaei, O. Sahin, J. Mol. Catal. A 385, 61 (2014)CrossRefGoogle Scholar
- 42.M.P. Lorenzo, J. Phys. Chem. Lett. 3, 167 (2012)CrossRefGoogle Scholar
- 43.H. Veisi, M. Ghadermazi, A. Naderi, Appl. Organomet. Chem. 30, 341 (2016)CrossRefGoogle Scholar
- 44.H. Veisi, M. Pirhayati, A. Kakanejadifard, Tetrahedron Lett. 58, 4269 (2017)CrossRefGoogle Scholar
- 45.J. Cookson, Platinum Met. Rev. 56, 83 (2012)CrossRefGoogle Scholar
- 46.L. Liang, A.K. Diallo, L. Salmon, J. Ruiz, D. Astruc, Eur. J. Inorg. Chem. 17, 2950 (2012)CrossRefGoogle Scholar
- 47.D.J. Gavia, Y.S. Shon, Langmuir 28, 14502 (2012)CrossRefGoogle Scholar
- 48.W. Zhang, X. Xiao, T. An, Z. Song, J. Fu, G. Sheng, M. Cui, J. Chem. Technol. Biotechnol. 78, 788 (2003)CrossRefGoogle Scholar
- 49.N. Mand, D.G. Crosby, J. Agric, Food Chem. 22, 849 (1974)CrossRefGoogle Scholar
- 50.Y.-T. Woo, D.Y. Lai, Aromatic Amino and Nitro-Amino Compounds and Their Halogenated Derivatives: Patty’s Toxicology (Wiley, New York, 2001)Google Scholar
- 51.Z.M. Wang, C.L. Xu, G.Q. Gao, X. Li, RSC Adv. 4, 13644 (2014)CrossRefGoogle Scholar
- 52.X.M. Chen, Z.X. Cai, X. Chen, M. Oyama, J. Mater. Chem. A 2, 5668 (2014)CrossRefGoogle Scholar
- 53.Z.F. Jiang, D.L. Jiang, A.M.S. Hossain, K. Qian, J.M. Xie, Z.F. Jiang, D.L. Jiang, A.M.S. Hossain, K. Qian, J.M. Xie, Phys. Chem. Chem. Phys. 17, 2550 (2015)CrossRefGoogle Scholar
- 54.V. Evangelista, B. Acosta, S. Miridonov, E. Smolentseva, S. Fuentes, A. Simakov, Appl. Catal. B 166–167, 518 (2015)CrossRefGoogle Scholar
- 55.Z.P. Dong, X. Le, C.X. Dong, W. Zhang, X.L. Li, J.T. Ma, Appl. Catal. B 162, 372 (2015)CrossRefGoogle Scholar
- 56.H.J.D. Dorman, S.G. Deans, J. Appl. Microbiol. 88, 308 (2000)CrossRefGoogle Scholar
- 57.A. Shtayeh, Z. Yaniv, J. Mahajna, J. Ethnopharmacol. 73, 221 (2000)CrossRefGoogle Scholar
- 58.G. Tümen, N. Ermin, T. Özek, M. Kürkçüoğlu, K.H.C. Başer, J. Essent. Oil Res. 6, 463 (1994)CrossRefGoogle Scholar
- 59.H. Veisi, A.R. Faraji, S. Hemmati, A. Gil, Appl. Organomet. Chem. 29, 517 (2015)CrossRefGoogle Scholar
- 60.H. Veisi, R. Ghorbani-Vaghei, S. Hemmati, M. Haji Aliani, T. Ozturk, Appl. Organomet. Chem 29, 26 (2015)CrossRefGoogle Scholar
- 61.S. Lebaschi, M. Hekmati, H. Veisi, J. Colloid. Interface Sci. 485, 223 (2017)CrossRefGoogle Scholar
- 62.H. Veisi, A. Rashtiani, V. Barjasteh, Appl. Organomet. Chem. 30, 231 (2016)CrossRefGoogle Scholar
- 63.. H. Veisi, N. Hajimoradian Nasrabadi, P. Mohammadi, Appl. Organomet. Chem. 30, 890 (2016)CrossRefGoogle Scholar
- 64.S.A. Aromal, V.K. Vidhu, D. Philip, Spectrochim. Acta A 85, 99 (2012)CrossRefGoogle Scholar
- 65.S.L. Cumberland, G.F. Strouse, Langmuir 18, 269 (2002)CrossRefGoogle Scholar
- 66.D.S. Sheny, J. Mathew, D. Philip, Spectrochim. Acta A 79, 254 (2011)CrossRefGoogle Scholar
- 67.D. Philip, C. Unni, Physica E 43, 1318 (2011)CrossRefGoogle Scholar
- 68.H. Kostova, S.C. Joe, J. Pinzaru, Optoelectron. Biomed. Mater. 1, 188 (2009)Google Scholar
- 69.H. Veisi, A. Khazaei, M. Safaei, D. Kordestani, J. Mol. Catal. A 382, 106 (2014)CrossRefGoogle Scholar
- 70.F. Bonyasi, M. Hekmati, H. Veisi, J. Colloid. Interface Sci. 496, 177 (2017)CrossRefGoogle Scholar
- 71.H. Veisi, A. Sedrpoushan, B. Maleki, M. Hekmati, M. Heidari, S. Hemmati, Appl. Organomet. Chem. 29, 834 (2015)CrossRefGoogle Scholar
- 72.H. Veisi, M. Hekmati, S. Hemmati, J. Heterocyclic. Chem 54, 1630 (2017)CrossRefGoogle Scholar
- 73.M. Hajighorbani, M. Hekmati, RSC Adv. 6, 88916 (2016)CrossRefGoogle Scholar
- 74.F. Heidari, M. Hekmati, H. Veisi, J. Colloid Interface Sci. 501, 175 (2017)CrossRefGoogle Scholar
- 75.M.H. Rashid, T.K. Mandal, J. Phys. Chem. C 111, 16750 (2007)CrossRefGoogle Scholar
- 76.N. Sahiner, H. Ozay, O. Ozay, N. Aktas, Appl. Catal. A 385, 201 (2010)CrossRefGoogle Scholar
- 77.N. Sahiner, H. Ozay, O. Ozay, N. Aktas, Appl. Catal. B 101, 137 (2010)CrossRefGoogle Scholar
- 78.N. Sahiner, O. Ozay, Curr. Nanosci. 8, 367 (2012)CrossRefGoogle Scholar
- 79.F.R. Fortea-Pérez, I. Schlegel, M. Julve, D. Armentano, G. De Munno, S.E. Stiriba, J. Organomet. Chem. 743, 102 (2013)CrossRefGoogle Scholar
- 80.Q.X. Liu, W. Zhang, X.J. Zhao, Z.X. Zhao, M.C. Shi, X.G. Wang, Eur. J. Org. Chem. 2013, 1253 (2013)CrossRefGoogle Scholar
- 81.M. Ghiaci, M. Zargani, F. Moeinpour, A. khojastehnezhad, Appl. Organomet. Chem. 28, 589 (2014)CrossRefGoogle Scholar
- 82.V.I. de Paula, C.A. Sato, R. Buffon, J. Braz. Chem. Soc. 23, 258 (2012)Google Scholar
- 83.S.M. Shakil Hussain, M.B. Ibrahim, A. Fazal, R. Suleiman, M. Fettouhi, B. El Ali, Polyhedron 70, 39 (2014)CrossRefGoogle Scholar
- 84.S. Sobhani, M.S. Ghasemzadeh, M. Honarmand, F. Zarifi, RSC Adv. 4, 44166 (2014)CrossRefGoogle Scholar
- 85.S. Sobhani, F. Zarifi, Chin. J. Catal. 36 555 (2015)CrossRefGoogle Scholar