Copper adorned magnetic nanoparticles as a heterogeneous catalyst for Sonogashira coupling reaction in aqueous media
Language English Country Great Britain, England Media electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
36289249
PubMed Central
PMC9606120
DOI
10.1038/s41598-022-22567-5
PII: 10.1038/s41598-022-22567-5
Knihovny.cz E-resources
- MeSH
- Bromides MeSH
- Iodides MeSH
- Magnetite Nanoparticles * MeSH
- Copper * chemistry MeSH
- Polyethylene Glycols MeSH
- Solvents MeSH
- Spectroscopy, Fourier Transform Infrared MeSH
- Water MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Bromides MeSH
- Iodides MeSH
- Magnetite Nanoparticles * MeSH
- Copper * MeSH
- Polyethylene Glycols MeSH
- Solvents MeSH
- Water MeSH
A nanomagnetic hydrophilic heterogeneous copper catalyst, termed γ-Fe2O3@PEG@PAMAM G0-Cu, has been successfully prepared and characterized using FT-IR, XRD, FE-SEM, TEM, EDX, mapping, TGA/DTG, VSM and ICP analyses. The catalyst displayed excellent activity for the palladium-free Sonogashira cross coupling reaction of various aryl iodides and bromides with phenylacetylene derivatives in pure water. The presence of polyethylene glycol coupled with hydrophilic character of the Cu-catalyst adorned on γ-Fe2O3 MNPs provides the ready dispersion of the catalyst particles in water, leading to higher catalytic performance as well as facile catalyst recovery via simple magnetic decantation. The recovered catalyst was reused for at least six successive runs with little reduction in its catalytic activity and any noticeable changes in its structure. The use of water as a green solvent, without requiring any additive or organic solvent, as well as the exploitation of abundant and low-cost copper catalyst instead of expensive Pd catalyst along with the catalyst recovery and scalability, make this method favorable from environmental and economic points of view for the Sonogashira coupling reaction.
See more in PubMed
Zimmerman JB, Anastas PT, Erythropel HC, Leitner W. Designing for a green chemistry future. Science. 2020;367:397–400. PubMed
Thathagar MB, Beckers J, Rothenberg G. Palladium-free and ligand-free Sonogashira cross-coupling. Green Chem. 2004;6:215–218.
Chen TL, Kim H, Pan SY, Tseng PC, Lin YP, Chiang PC. Implementation of green chemistry principles in circular economy system towards sustainable development goals: Challenges and perspectives. Sci. Total Environ. 2020;716:136998. PubMed
Zhang W, Cue BW. Green Techniques for Organic Synthesis and Medicinal Chemistry. Wiley; 2018.
Destito P, Vidal C, López F, Mascareñas JL. Transition metal-promoted reactions in aqueous media and biological settings. Chem. Eur. J. 2021;27:4789–4816. PubMed
C. M. Eichenseer, B. Kastl, M. A. Pericàs, P. R. Hanson & O. Reiser. ACS Sustain. Chem. Eng. 4, 2698-2705 (2016).
Baig RN, Varma RS. Magnetically retrievable catalysts for organic synthesis. ChemComm. 2013;49:752–770. PubMed
Baig RN, Varma RS. Organic synthesis via magnetic attraction: Benign and sustainable protocols using magnetic nanoferrites. Green Chem. 2013;15:398–417.
Joshi R, Singh BP, Prajapat C, Kashyap Y, Nayak C, Bhattacharyya DRS. Ningthoujam, insights into the structural and microscopic origin of magnetic properties of the γ-Fe2O3@MnxOy nanostructure. J. Phys. Chem. C. 2021;125:17971–17982.
Simon MO, Li CJ. Green chemistry oriented organic synthesis in water. Chem. Soc. Rev. 2012;41:1415–1427. PubMed
Li C-J, Chen L. Organic chemistry in water. Chem. Soc. Rev. 2006;35:68–82. PubMed
Nasrollahzadeh M, Motahharifar N, Ghorbannezhad F, Bidgoli NSS, Baran T, Varma RS. Recent advances in polymer supported palladium complexes as (nano) catalysts for Sonogashira coupling reaction. Mol. Catal. 2020;480:110645.
Shin H, Suh Y, Lim D. Recent progress in plasmonic hybrid photocatalysis for CO2 photoreduction and C–C coupling reactions. Catalysts. 2021;11:155.
Lee NR, Cortes-Clerget M, Wood AB, Lippincott DJ, Pang H, Moghadam FA, Gallou F, LipshutzCoolade BH. A low-foaming surfactant for organic synthesis in water. Chemsuschem. 2019;12:3159–3165. PubMed
Nasseri MA, Rezazadeh Z, Kazemnejadi M, Allahresani A. A Co–Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C–N cross-coupling reactions in water. Dalton Trans. 2020;49:10645–10660. PubMed
Parandhaman T, Pentela N, Ramalingam B, Samanta D, Das SK. Metal nanoparticle loaded magnetic-chitosan microsphere: Water dispersible and easily separable hybrid metal nano-biomaterial for catalytic applications. ACS Sustain. Chem. Eng. 2017;5:489–501.
Motahharifar N, Nasrollahzadeh M, Taheri-Kafrani A, Varma RS, Shokouhimehr M. Magnetic chitosan-copper nanocomposite: A plant assembled catalyst for the synthesis of amino-and N-sulfonyl tetrazoles in eco-friendly media. Carbohydr. Polym. 2020;232:115819. PubMed
Baig RN, Varma RS. Copper on chitosan: A recyclable heterogeneous catalyst for azide–alkyne cycloaddition reactions in water. Green Chem. 2013;15:1839–1843.
Vaddula BR, Saha A, Varma RS, Leazer J. Tsuji-Trost N-allylation with allylic acetates by using a cellulose-palladium catalyst. Eur. J. Org. Chem. 2012;2012:6707–6709.
Kou J, Saha A, Bennett-Stamper C, Varma RS. Inside-out core–shell architecture: controllable fabrication of Cu2O@Cu with high activity for the Sonogashira coupling reaction. ChemComm. 2012;48:5862–5864. PubMed
Yuan Y, Zhu H, Zhao D, Zhang L. Ligand-free copper oxide nanoparticle-catalyzed sonogashira coupling reaction. Synthesis. 2011;2011:1792–1798.
Biffis A, Scattolin E, Ravasio N, Zaccheria F. Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions. Tetrahedron Lett. 2007;48:8761–8764.
Arundhathi R, Damodara D, Mohan KV, Kantam ML, Likhar PR. Monodispersed and stable nano copper (0) from copper-aluminium hydrotalcite: Importance in C–C couplings of deactivated aryl chlorides. Adv. Synth. Catal. 2013;355:751–756.
Mitrofanov AY, Murashkina AV, Martín-García I, Alonso F, Beletskaya IP. Formation of C-C, C–S and C–N bonds catalysed by supported copper nanoparticles. Catal. Sci. Technol. 2017;7(19):4401–4412.
Al-Zoubi RM, Al-Omari MK, Al-Jammal WK, Ferguson MJ. Palladium-catalyzed highly regioselective mono and double Sonogashira cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under ambient conditions. RSC Adv. 2020;10:16366–16376. PubMed PMC
Budarin V, Shuttleworth P, Clark J, Luque R. Industrial applications of CC coupling reactions. Curr. Org. Synth. 2010;7:614–627.
Colacot TJ. The 2010 Nobel Prize in chemistry: Palladium-catalysed cross-coupling. Platin. Met. Rev. 2011;55:84–90.
Sonogashira K, Tohda Y, Hagihara N. A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett. 1975;16:4467–4470.
Ferlin F, Valentini F, Sciosci D, Calamante M, Petricci E, Vaccaro L. Biomass waste-derived Pd-PiNe catalyst for the continuous-flow copper-free sonogashira reaction in a CPME-water azeotropic mixture. ACS Sustain. Chem. Eng. 2021;9:12196–12204.
Tan E, Quinonero O, ElenadeOrbe M, Echavarren AM. Broad-scope Rh-catalyzed inverse-Sonogashira reaction directed by weakly coordinating groups. ACS Catal. 2018;8:2166–2172. PubMed PMC
Mohajer F, Heravi MM, Zadsirjan V, Poormohammad N. Copper-free Sonogashira cross-coupling reactions: An overview. RSC Adv. 2021;11(12):6885–6925. PubMed PMC
Nasseri MA, Rezazadeh Z, Kazemnejadi M, Allahresani A. Magnetic Cu–Schiff base complex with an ionic tail as a recyclable bifunctional catalyst for base/Pd-free Sonogashira coupling reaction. J. Iran. Chem. Soc. 2019;16(12):2693–2705.
Sobhani S, Pakdin-Parizi Z. Palladium-DABCO complex supported on γ-Fe2O3 magnetic nanoparticles: A new catalyst for CC bond formation via Mizoroki-Heck cross-coupling reaction. Appl. Catal. A Gen. 2014;479:112–120.
Zomorodian K, Veisi H, Mousavi SM, Ataabadi MS, Yazdanpanah S, Bagheri J, Mehr AP, Hemmati S, Veisi H. Modified magnetic nanoparticles by PEG-400-immobilized Ag nanoparticles (Fe3O4@PEG–Ag) as a core/shell nanocomposite and evaluation of its antimicrobial activity. Int. J. Nanomed. 2018;13:3965. PubMed PMC
Nasseri MA, Allahresani A, Esmaeili AA. Niobium pentachloride catalyzed one-pot multicomponent condensation reaction of β-naphthol, aryl aldehydes and cyclic 1, 3-dicarbonyl compounds. Lett. Org. Chem. 2014;11:91–96.
White BR, Stackhouse BT, Holcombe JA. Magnetic γ-Fe2O3 nanoparticles coated with poly-l-cysteine for chelation of As (III), Cu (II), Cd (II), Ni (II), Pb (II) and Zn (II) J. Hazard. Mater. 2009;161:848–853. PubMed
Chang M, Chang YJ, Chao PY, Yu Q. Exosome purification based on PEG-coated Fe3O4 nanoparticles. PLoS ONE. 2018;13:e0199438. PubMed PMC
Sardarian AR, Eslahi H, Esmaeilpour M. Green, cost-effective and efficient procedure for Heck and Sonogashira coupling reactions using palladium nanoparticles supported on functionalized Fe3O4@SiO2 by polyvinyl alcohol as a highly active, durable and reusable catalyst. Appl. Organomet. Chem. 2019;33:e4856.
Mohammadinezhad A, Akhlaghinia B. Fe3O4@Boehmite-NH2-CoII NPs: An inexpensive and highly efficient heterogeneous magnetic nanocatalyst for the Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions. Green Chem. 2017;19:5625–5641.
Murugan E, Jebaranjitham JN. Dendrimer grafted core–shell Fe3O4–polymer magnetic nanocomposites stabilized with AuNPs for enhanced catalytic degradation of Rhodamine B–a kinetic study. J. Chem. Eng. 2015;259:266–276.
Kühbeck D, Saidulu G, Reddy KR, Díaz DD. Critical assessment of the efficiency of chitosan biohydrogel beads as recyclable and heterogeneous organocatalyst for C–C bond formation. Green chem. 2012;14:378–392.
Sardarian AR, Kazemnejadi M, Esmaeilpour M. Bis-salophen palladium complex immobilized on Fe3O4@SiO2 nanoparticles as a highly active and durable phosphine-free catalyst for Heck and copper-free Sonogashira coupling reactions. Dalton Trans. 2019;48:3132–3145. PubMed
Jiang Y, Jiang J, Gao Q, Ruan M, Yu H, Qi L. A novel nanoscale catalyst system composed of nanosized Pd catalysts immobilized on Fe3O4@SiO2–PAMAM. Nanotechnology. 2008;19:075714. PubMed
Baran NY, Baran T, Menteş A. Design of highly robust halloysite nanoclay supported palladium complex as a highly active heterogeneous catalyst for construction of biaryls. Appl. Clay Sci. 2019;181:105225.
Darezereshki E. Synthesis of maghemite (γ-Fe2O3) nanoparticles by wet chemical method at room temperature. Mater. Lett. 2010;64:1471–1472.
Sreeja V, Joy P. Microwave–hydrothermal synthesis of γ-Fe2O3 nanoparticles and their magnetic properties. Mater. Res. Bull. 2007;42:1570–1576.
Liu Y, Blanchard V, Danoun G, Zhang Z, Tlili A, Zhang W, Monnier F, Van Der Lee A, Mao J, Taillefer M. Copper-catalyzed sonogashira reaction in water. ChemistrySelect. 2017;2:11599–11602.
Liori AA, Stamatopoulos IK, Papastavrou AT, Pinaka A, Vougioukalakis GC. A sustainable, user-friendly protocol for the Pd-free sonogashira coupling reaction. Eur. J. Org. Chem. 2018;2018:6134–6139.
Song JY, Zhou X, Song H, Liu Y, Zhao HY, Sun ZZ, Chu WY. Visible-light-assisted cobalt-2-(hydroxyimino)-1-phenylpropan-1-one complex catalyzed Pd/Cu-free Sonogashira-Hagihara cross-coupling reaction. ChemCatChem. 2018;10:758–762.
Hajipour AR, Rezaei F, Khorsandi Z. Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst. Green Chem. 2017;19:1353–1361.
Li Y, Feng X, Li Z. Visible-light-initiated Sonogashira coupling reactions over CuO/TiO2 nanocomposites. Catal. Sci. Technol. 2019;9:377–383.
Wang B, Wang Y, Li J, Guo X, Bai G, Tong X, Jin G, Guo X. Photocatalytic Sonogashira reaction over silicon carbide supported Pd–Cu alloy nanoparticles under visible light irradiation. Catal. Sci. Technol. 2018;8:3357–3362.
Beletskaya IP, Cheprakov AV. Copper in cross-coupling reactions: The post-Ullmann chemistry. Coord. Chem. Rev. 2004;248:2337–2364.
Li JH, Li JL, Wang DP, Pi S-F, Xie YX, Zhang MB, Hu XC. CuI-catalyzed Suzuki−Miyaura and Sonogashira cross-coupling reactions using DABCO as ligand. Coord. Chem. Rev. 2007;72:2053–2057. PubMed
Oka H, Kitai K, Suzuki T, Obora Y. N, N-Dimethylformamide-stabilized copper nanoparticles as a catalyst precursor for Sonogashira-Hagihara cross coupling. RSC Adv. 2017;7:22869–22874.