Abstract
An eco-friendly approach is described for the generation of Ni nanoparticles on a magnetized cellulose biopolymer wherein the adorned biopolymer mimics a core–shell type nanocomposite (Fe3O4@CNF@Ni) is realized via sonication. The physicochemical and morphological specifications of the ensued nanocomposite were characterized using various advanced techniques like FT-IR, FESEM, TEM, EDX, VSM, BET-BJH, DLS, XRD, TGA, XPS and ICP-OES. The catalytic performance of the Fe3O4@CNF@Ni was evaluated in the ultrasound-assisted classical Hiyama and Suzuki–Miyaura cross-coupling reactions for the synthesis of a variety of biaryl derivatives; superior performance was discerned for both the protocols where sonication played a vital role relative to conventional heating for expeditious reaction, easier work-up and higher yields. Hot filtration and Hg toxication tests for the nanocomposite, Fe3O4@CNF@Ni revealed higher stability, and low metal leaching. Its heterogeneous nature as the magnetically retrievable catalyst could be ascertained by reuse in up to seven successive cycles without significant loss of efficacy.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Alamgholiloo H, Rostamnia S, Zhang K et al (2020) Boosting aerobic oxidation of alcohols via synergistic effect between TEMPO and a composite Fe3O4/Cu-BDC/GO nanocatalyst. ACS Omega 5:5182–5191. https://doi.org/10.1021/acsomega.9b04209
Allahyari S, Haghighi M, Ebadi A, Hosseinzadeh S (2014) Ultrasound assisted co-precipitation of nanostructured CuO–ZnO–Al2O3 over HZSM-5: effect of precursor and irradiation power on nanocatalyst properties and catalytic performance for direct syngas to DME. Ultrason Sonochem 21:663–673. https://doi.org/10.1016/j.ultsonch.2013.09.014
Ashraf MA, Liu Z, Peng W-X, Zhou L (2020) Glycerol Cu(II) complex supported on Fe3O4 magnetic nanoparticles: a new and highly efficient reusable catalyst for the formation of aryl-sulfur and aryl-oxygen bonds. Catal Lett 150:1128–1141. https://doi.org/10.1007/s10562-019-02973-7
Bagherzade G, Khashei Siuki H, Ghamari Kargar P (2021) Use of pectin as a suitable substrate for catalyst synthesis Fe3O4@Pectin@Ni (II) and its application in oxidation reaction. Medbiotech J 5:1–8. https://doi.org/10.22034/mbt.2021.135147
Baig RBN, Varma RS (2013) Magnetically retrievable catalysts for organic synthesis. Chem Commun 49:752–770. https://doi.org/10.1039/C2CC35663E
Bakherad M, Ali Keivanloo A, Amin AM, Ghamari Kargar P (2018) Silica-anchored Cu(I) aminothiophenol complex: an efficient heterogeneous catalyst for synthesis of 1,4-disubstituted 1,2,3-triazoles in water. Iran J Catal 8(3):179–187
Bakhshi O, Bagherzade G, Ghamari Kargar P (2021) Biosynthesis of organic nanocomposite using Pistacia vera L. Hull: an efficient antimicrobial agent. Bioinorg Chem Appl 2021:1–18. https://doi.org/10.1155/2021/4105853
Baran T (2018) Ultrasound-accelerated synthesis of biphenyl compounds using novel Pd(0) nanoparticles immobilized on bio-composite. Ultrason Sonochem 45:231–237. https://doi.org/10.1016/j.ultsonch.2018.03.017
Baran T (2019) Highly recoverable, reusable, cost-effective, and Schiff base functionalized pectin supported Pd(II) catalyst for microwave-accelerated Suzuki cross-coupling reactions. Int J Biol Macromol 127:232–239. https://doi.org/10.1016/j.ijbiomac.2019.01.046
Baran T, Menteş A (2016) Microwave assisted synthesis of biarlys by CC coupling reactions with a new chitosan supported Pd(II) catalyst. J Mol Struct 1122:111–116. https://doi.org/10.1016/j.molstruc.2016.05.091
Baran T, Sargin I, Kaya M, Menteş A (2016) An environmental catalyst derived from biological waste materials for green synthesis of biaryls via Suzuki coupling reactions. J Mol Catal A Chem 420:216–221. https://doi.org/10.1016/j.molcata.2016.04.025
Bhattacharyya B, Biswas JP, Mishra S, Gogoi N (2019) Rapid Suzuki–Miyaura cross-coupling reaction catalyzed by zirconium carboxyphosphonate supported mixed valent Pd(0)/Pd(II) catalyst. Appl Organomet Chem. https://doi.org/10.1002/aoc.5017
Budiman YP, Friedrich A, Radius U, Marder TB (2019) Copper-catalysed Suzuki–Miyaura cross-coupling of highly fluorinated aryl boronate esters with aryl iodides and bromides and fluoroarene−arene π-stacking interactions in the products. ChemCatChem 11:5387–5396. https://doi.org/10.1002/cctc.201901220
Çalışkan M, Baran T (2022) Immobilized palladium nanoparticles on Schiff base functionalized ZnAl layered double hydroxide: a highly stable and retrievable heterogeneous nanocatalyst towards aryl halide cyanations. Appl Clay Sci 219:106433. https://doi.org/10.1016/j.clay.2022.106433
Çalışkan M, Baran T, Nasrollahzadeh M (2021) Facile preparation of nanostructured Pd-Sch-δ-FeOOH particles: a highly effective and easily retrievable catalyst for aryl halide cyanation and p-nitrophenol reduction. J Phys Chem Solids 152:109968. https://doi.org/10.1016/j.jpcs.2021.109968
Chen Y, Wang M, Zhang L et al (2017) Poly(o-aminothiophenol)-stabilized Pd nanoparticles as efficient heterogenous catalysts for Suzuki cross-coupling reactions. RSC Adv 7:47104–47110. https://doi.org/10.1039/C7RA09947A
Chen M, Wang W, Li Y (2019) N-heterocyclic carbene–palladium complexes for Suzuki–Miyaura coupling reaction with benzyl chloride and aromatic boronic acid leading to diarylmethanes. Appl Organomet Chem 33:e4912. https://doi.org/10.1002/aoc.4912
Cho SH, Kim JY, Kwak J, Chang S (2011) Recent advances in the transition metal-catalyzed twofold oxidative C–H bond activation strategy for C–C and C–N bond formation. Chem Soc Rev 40:5068. https://doi.org/10.1039/c1cs15082k
Dindarloo Inaloo I, Majnooni S, Eslahi H, Esmaeilpour M (2020) Air-stable Fe3O4@SiO2-EDTA-Ni(0) as an efficient recyclable magnetic nanocatalyst for effective Suzuki–Miyaura and heck cross-coupling via aryl sulfamates and carbamates. Appl Organomet Chem. https://doi.org/10.1002/aoc.5662
Donegan KP, Godsell JF, Otway DJ et al (2012) Size-tuneable synthesis of nickel nanoparticles. J Nanoparticle Res 14:670. https://doi.org/10.1007/s11051-011-0670-y
Feizi Mohazzab B, Jaleh B, Issaabadi Z et al (2019) Stainless steel mesh-GO/Pd NPs: catalytic applications of Suzuki–Miyaura and stille coupling reactions in eco-friendly media. Green Chem 21:3319–3327. https://doi.org/10.1039/C9GC00889F
Ghamari Kargar P, Bagherzade G (2021a) A green synthesis strategy of binuclear catalyst for the C–C Cross-coupling reactions in the aqueous medium: Hiyama and Suzuki–Miyaura reactions as case studies. Front Chem. https://doi.org/10.3389/fchem.2021.747016
Ghamari Kargar P, Bagherzade G (2021) The anchoring of a Cu(ii)–salophen complex on magnetic mesoporous cellulose nanofibers: green synthesis and an investigation of its catalytic role in tetrazole reactions through a facile one-pot route. RSC Adv 11:19203–19220. https://doi.org/10.1039/D1RA01913A
Ghamari Kargar P, Bagherzade G (2021b) Robust, highly active, and stable supported Co(ii) nanoparticles on magnetic cellulose nanofiber-functionalized for the multi-component reactions of piperidines and alcohol oxidation. RSC Adv 11:23192–23206. https://doi.org/10.1039/D1RA00208B
Ghamari Kargar P, Aryanejad S, Bagherzade G (2020a) Simple synthesis of the novel Cu–MOF catalysts for the selective alcohol oxidation and the oxidative cross-coupling of amines and alcohols. Appl Organomet Chem. https://doi.org/10.1002/aoc.5965
Ghamari Kargar P, Bagherzade G, Eshghi H (2020b) Novel biocompatible core/shell Fe3O4@NFC@Co( ii ) as a new catalyst in a multicomponent reaction: an efficient and sustainable methodology and novel reusable material for one-pot synthesis of 4 H -pyran and pyranopyrazole in aqueous media. RSC Adv 10:37086–37097. https://doi.org/10.1039/D0RA04698A
Ghamari Kargar P, Bagherzade G, Eshghi H (2020) Design and synthesis of magnetic Fe3O4@NFC-ImSalophCu nanocatalyst based on cellulose nanofibers as a new and highly efficient, reusable, stable and green catalyst for the synthesis of 1,2,3-triazoles. RSC Adv 10:32927–32937. https://doi.org/10.1039/D0RA06251K
Ghamari Kargar P, Ghasemi M, Bagherzade G (2021a) Copper (II) supported on a post-modified magnetic Pectin Fe3O4@Pectin–Imidazole–SO3H–Cu(II): an efficient biopolymer-based catalyst for selective oxidation of alcohols with aqueous TBHP. Sci Iran. https://doi.org/10.24200/sci.2021.58355.5689
Ghamari Kargar P, Noorian M, Chamani E et al (2021b) Synthesis, characterization and cytotoxicity evaluation of a novel magnetic nanocomposite with iron oxide deposited on cellulose nanofibers with nickel (Fe3O4@NFC@ONSM-Ni). RSC Adv 11:17413–17430. https://doi.org/10.1039/D1RA01256H
Ghamari Kargar P, Ravanjamjah A, Bagherzade G (2021c) A novel water-dispersible and magnetically recyclable nickel nanoparticles for the one-pot reduction-Schiff base condensation of nitroarenes in pure water. J Chin Chem Soc 68:1916–1933. https://doi.org/10.1002/jccs.202100172
Ghamari Kargar P, Bagherzade G, Eshghi H (2021) Introduction of a trinuclear manganese(iii) catalyst on the surface of magnetic cellulose as an eco-benign, efficient and reusable novel heterogeneous catalyst for the multi-component synthesis of new derivatives of xanthene. RSC Adv 11:4339–4355. https://doi.org/10.1039/D0RA09420J
Ghamari Kargar P, Bagherzade G, Beyzaei H (2022a) A porous metal-organic framework (Ni-MOF): an efficient and recyclable catalyst for cascade oxidative amidation of alcohols by amines under ultrasound-irradiations. Mol Catal 526:112372. https://doi.org/10.1016/j.mcat.2022.112372
Ghamari Kargar P, Len C, Luque R (2022b) Cu/cellulose-modified magnetite nanocomposites as a highly active and selective catalyst for ultrasound-promoted aqueous O-arylation Ullmann and sp-sp2 Sonogashira cross-coupling reactions. Sustain Chem Pharm 27:100672. https://doi.org/10.1016/j.scp.2022.100672
Ghamari Kargar P, Bagherzade G, Beyzaei H, Arghavani S (2022) BioMOF–Mn: an antimicrobial agent and an efficient nanocatalyst for domino one-pot preparation of xanthene derivatives. Inorg Chem. https://doi.org/10.1021/acs.inorgchem.2c00819
Ghanbari N, Hoseini SJ, Bahrami M (2017) Ultrasonic assisted synthesis of palladium-nickel/iron oxide core–shell nanoalloys as effective catalyst for Suzuki–Miyaura and p-nitrophenol reduction reactions. Ultrason Sonochem 39:467–477. https://doi.org/10.1016/j.ultsonch.2017.05.015
Hiyama T (2002) How I came across the silicon-based cross-coupling reaction. J Organomet Chem 653:58–61. https://doi.org/10.1016/S0022-328X(02)01157-9
Hooshmand SE, Heidari B, Sedghi R, Varma RS (2019) Recent advances in the Suzuki–Miyaura cross-coupling reaction using efficient catalysts in eco-friendly media. Green Chem 21:381–405. https://doi.org/10.1039/C8GC02860E
Johansson Seechurn CCC, Kitching MO, Colacot TJ, Snieckus V (2012) Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 nobel prize. Angew Chemie Int Ed 51:5062–5085. https://doi.org/10.1002/anie.201107017
Kandathil V, Siddiqa A, Patra A et al (2020) NHC-Pd complex heterogenized on graphene oxide for cross-coupling reactions and supercapacitor applications. Appl Organomet Chem. https://doi.org/10.1002/aoc.5924
Khashei Siuki H, Bagherzade G, Ghamari Kargar P (2020) A green method for synthesizing nickel nanoparticles supported by magnetized pectin: applied as a catalyst for aldehyde synthesis as a precursor in xanthan synthesis. ChemistrySelect 5:13537–13544. https://doi.org/10.1002/slct.202002946
Khashei Siuki H, Ghamari Kargar P, Bagherzade G (2022) New acetamidine Cu(II) Schiff base complex supported on magnetic nanoparticles pectin for the synthesis of triazoles using click chemistry. Sci Rep 12:3771. https://doi.org/10.1038/s41598-022-07674-7
Mesganaw T, Garg NK (2013) Ni- and Fe-catalyzed cross-coupling reactions of phenol derivatives. Org Process Res Dev 17:29–39. https://doi.org/10.1021/op300236f
Mirza-Aghayan M, Ganjbakhsh N, Molaee Tavana M, Boukherroub R (2016) Ultrasound-assisted direct oxidative amidation of benzyl alcohols catalyzed by graphite oxide. Ultrason Sonochem 32:37–43. https://doi.org/10.1016/j.ultsonch.2016.02.017
Mohammadi Metkazini SF, Khorsandi Z, Heydari A, Varma RS (2021) Sustainable visible light-driven heck and suzuki reactions using NiCu nanoparticles adorned on carbon nano-onions. ACS Sustain Chem Eng 9:14061–14069. https://doi.org/10.1021/acssuschemeng.1c03499
Namboodiri VV, Varma RS (2001) Microwave-accelerated Suzuki cross-coupling reaction in polyethylene glycol (PEG). Green Chem 3:146–148. https://doi.org/10.1039/b102337n
Nasir Baig RB, Varma RS (2013) Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites. Green Chem 15:398–417. https://doi.org/10.1039/C2GC36455G
Nasrollahzadeh M, Issaabadi Z, Varma RS (2019) Magnetic lignosulfonate-supported Pd complex: renewable resource-derived catalyst for aqueous Suzuki–Miyaura reaction. ACS Omega 4:14234–14241. https://doi.org/10.1021/acsomega.9b01640
Nasrollahzadeh M, Ghorbannezhad F, Varma RS (2020a) Ultrasound-assisted fabrication of N-cyano-N-arylbenzenesulfonamides at ambient temperature: improvements with biosynthesized Ag/feldspar nanocomposite. Clean Technol Environ Policy 22:231–246. https://doi.org/10.1007/s10098-019-01779-w
Nasrollahzadeh M, Motahharifar N, Ghorbannezhad F et al (2020b) Recent advances in polymer supported palladium complexes as (nano)catalysts for Sonogashira coupling reaction. Mol Catal 480:110645. https://doi.org/10.1016/j.mcat.2019.110645
Ohtaka A, Sansano JM, Nájera C et al (2015) Palladium and bimetallic palladium-nickel nanoparticles supported on multiwalled carbon nanotubes: application to carbon–carbon bond-forming reactions in water. ChemCatChem 7:1841–1847. https://doi.org/10.1002/cctc.201500164
Özhava D, Kılıçaslan NZ, Özkar S (2015) PVP-stabilized nickel(0) nanoparticles as catalyst in hydrogen generation from the methanolysis of hydrazine borane or ammonia borane. Appl Catal B Environ 162:573–582. https://doi.org/10.1016/j.apcatb.2014.07.033
Pagliaro M, Pandarus V, Ciriminna R et al (2012) Heterogeneous versus homogeneous palladium catalysts for cross-coupling reactions. ChemCatChem 4:432–445. https://doi.org/10.1002/cctc.201100422
Piontek A, Bisz E, Szostak M (2018) Iron-catalyzed cross-couplings in the synthesis of pharmaceuticals. In pursuit of sustainability. Angew Chemie Int Ed 57:11116–11128. https://doi.org/10.1002/anie.201800364
Rathi AK, Gawande MB, Ranc V et al (2016) Continuous flow hydrogenation of nitroarenes, azides and alkenes using maghemite–Pd nanocomposites. Catal Sci Technol 6:152–160. https://doi.org/10.1039/C5CY00956A
Sancheti SV, Gogate PR (2018) Intensification of heterogeneously catalyzed Suzuki–Miyaura cross-coupling reaction using ultrasound: understanding effect of operating parameters. Ultrason Sonochem 40:30–39. https://doi.org/10.1016/j.ultsonch.2017.01.037
Sedghi R, Heidari B, Shahmohamadi H et al (2019) Pd Nanocatalyst adorned on magnetic chitosan@N-heterocyclic carbene: eco-compatible suzuki cross-coupling reaction. Molecules 24:3048. https://doi.org/10.3390/molecules24173048
Shokouhimehr M, Hong K, Lee TH et al (2018) Magnetically retrievable nanocomposite adorned with Pd nanocatalysts: efficient reduction of nitroaromatics in aqueous media. Green Chem 20:3809–3817. https://doi.org/10.1039/C8GC01240G
Suzuki A (1985) Organoboron compounds in new synthetic reactions. Pure Appl Chem 57:1749–1758. https://doi.org/10.1351/pac198557121749
Varma RS (2008) Chemical activation by mechanochemical mixing, microwave and ultrasonic irradiation. Green Chem 10:1129. https://doi.org/10.1039/b817559b
Varma RS (2019) Biomass-derived renewable carbonaceous materials for sustainable chemical and environmental applications. ACS Sustain Chem Eng 7:6458–6470. https://doi.org/10.1021/acssuschemeng.8b06550
Veisi H, Joshani Z, Karmakar B et al (2021) Ultrasound assisted synthesis of Pd NPs decorated chitosan-starch functionalized Fe3O4 nanocomposite catalyst towards Suzuki–Miyaura coupling and reduction of 4-nitrophenol. Int J Biol Macromol 172:104–113. https://doi.org/10.1016/j.ijbiomac.2021.01.040
Yung T-Y, Huang L-Y, Chan T-Y et al (2014) Synthesis and characterizations of Ni–NiO nanoparticles on PDDA-modified graphene for oxygen reduction reaction. Nanoscale Res Lett 9:444. https://doi.org/10.1186/1556-276X-9-444
Acknowledgments
We gratefully acknowledge the University of Birjand, and Amirkabir University of Technology for the support of this work. The participation and generous contribution of all our collaborators over the years is appreciated.
Funding
The authors have not disclosed any funding.
Author information
Authors and Affiliations
Contributions
Conceptualization, Investigation, Resources, Writing–original draft: PGK; Performing and conducting the experiment, Data curation, and revising the draft: MN; Contributing to preforming the experiment, Formal analysis, and editing the article: ZP; Project and concept Supervision, revised and review manuscript (final draft and revised version): RSV.
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Ghamari Kargar, P., Nayebi, M., Parhizi, Z. et al. Nickel nanoparticles adorned on magnetized cellulose nanofibers: ultrasound-facilitated cross coupling reactions. Cellulose 29, 9183–9198 (2022). https://doi.org/10.1007/s10570-022-04823-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-022-04823-z