Imidazolium chloride-Co(<scp>iii</scp>) complex immobilized on Fe3O4@SiO2 as a highly active bifunctional nanocatalyst for the copper-, phosphine-, and base-free Heck and Sonogashira reactions

Kazemnejadi, Milad; Alavi, G Seyyedeh Ameneh; Rezazadeh, Zinat; Nasseri, Mohammad Ali; Allahresani, Ali; Esmaeilpour, Mohsen

doi:10.1039/c8gc03919d

Cited by 53 publications

(42 citation statements)

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“…The results showed that consecutive functionalization of the nanoparticles by silicate and chlorophyll groups did not change the phase and structure of the Fe 3 O 4 core, and no shifts were observed at peak angles (Figure 4c). [ 41,46 ] The four peaks appearing in 28.7°, 40.7°, 66.7°, and 50.4° corresponded to the crystalline phase of the chlorophyll decorated on the Fe 3 O 4 @SiO 2 nanoparticles.…”

Section: Resultsmentioning

confidence: 99%

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Mg‐catalyzed one‐pot preparation of benzimidazoles and spirooxindoles by an immobilized chlorophyll b on magnetic nanoparticles

Shamaei

Mahmoudi

Kazemnejadi

et al. 2020

Applied Organom Chemis

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Chlorophyll b was extracted from Heliotropium europaeum plant, then immobilized on magnetic nanoparticles (Fe3O4@SiO2@Chl‐Mg) and found as an efficient and green catalyst for the preparation of a variety of benzimidazoles and spirooxindoles in mild conditions. The catalyst was fully characterized by Fourier‐transform infrared (FTIR), ultraviolet–visible (UV–vis) spectroscopy, X‐ray diffraction (XRD), energy‐dispersive X‐ray spectroscopy (EDX), thermogravimetric (TGA), vibrating sample magnetometer (VSM), transmission electron microscopy (TEM), and dynamic light scattering (DLS) analyses. To prove the catalytic influence of Mg over the reactions, the catalytic activity of the demetalated chlorophyll b as well as some other control experiments was investigated. High to excellent yields were achieved for all entries, whether benzimidazole or spirooxindole derivatives at short reaction times. The catalyst could be recovered and reused for several consecutive runs by a simple external magnetic field without any considerable reactivity loss. The properties of the recovered catalyst were investigated by various analyses. Finally, the reasonable mechanisms were proposed for the reactions based on the literature.

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Section: Resultsmentioning

confidence: 99%

“…Fe 3 O 4 @SiO 2 NPs were prepared according to a co‐precipitation method followed by coating with silica shell that was previously reported elsewhere. [ 40,41 ]…”

Section: Methodsmentioning

confidence: 99%

Mg‐catalyzed one‐pot preparation of benzimidazoles and spirooxindoles by an immobilized chlorophyll b on magnetic nanoparticles

Shamaei

Mahmoudi

Kazemnejadi

et al. 2020

Applied Organom Chemis

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“…On the other hand, there are few composites which have the constitutes that chemically interact with each other. Graphene oxide, polyethylene glycol, polyethyleneimine, allyl calixarene, and polymerized cobalt(III) complex are involved in the chemical interaction with FSs during the formation of FS composites . The non‐FSs have formed the composites with the polymers containing significant functional groups.…”

Section: Composites As Fssmentioning

confidence: 99%

“…While iron(III) FS catalyst is useful in the cross‐coupling reaction between olefins and aryl iodides, nickel(II) FS catalyst promotes the Kumada‐Corriu reaction . Cobalt(III) FS is reported to be a catalyst for Heck‐Mizoroki and Sonogashira couplings . Of note, the first row transition metal FS catalysts are seen as the affordable substitutes for the costly noble palladium catalysts in C−C coupling reactions…”

Section: Applications and Advantages Of Fs‐based Catalystsmentioning

confidence: 99%

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Antony

Marimuthu

Yang

et al. 2019

The Chemical Record

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Heterogeneous catalysis plays a key role in promoting green chemistry through many routes. The functionalizable reactive silanols highlight silica as a beguiling support for the preparation of heterogeneous catalysts. Metal active sites anchored on functionalized silica (FS) usually demonstrate the better dispersion and stability due to their firm chemical interaction with FSs. Having certain functional groups in structure, FSs can act as the useful catalysts for few organic reactions even without the need of metal active sites which are termed as the covetous reusable organocatalysts. Magnetic FSs have laid the platform where the effortless recovery of catalysts is realized just using an external magnet, resulting in the simplified reaction procedure. Using FSs of multiple functional groups, we can envisage the shortened reaction pathway and, reduced chemical uses and chemical wastes. Unstable bio‐molecules like enzymes have been stabilized when they get chemically anchored on FSs. The resultant solid bio‐catalysts exhibited very good reusability in many catalytic reactions. Getting provoked from the green chemistry aspects and benefits of FS‐based catalysts, we confer the recent literature and progress focusing on the significance of FSs in heterogeneous catalysis. This review covers the preparative methods, types and catalytic applications of FSs. A special emphasis is given to the metal‐free FS catalysts, multiple FS‐based catalysts and magnetic FSs. Through this review, we presume that the contribution of FSs to green chemistry can be well understood. The future perspective of FSs and the improvements still required for implementing FS‐based catalysts in practical applications have been narrated at the end of this review.

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“…Magnetically recoverable catalysts can be utilized in a wide range of reactions. Magnetic nanoparticle surfaces can be tailored for a specific application by designing a specific surface activation, thus resulting in versatile carriers [36][37][38][39][40][41] . Developments in the immobilization of enzymes can improve the stability and activity of enzymes and expand the range of conditions in which the enzymes can be used by significantly increasing the total turnover number and significantly improving the overall process efficiency 42 .…”

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confidence: 99%

Reduction of nitroarenes by magnetically recoverable nitroreductase immobilized on Fe3O4 nanoparticles

Zhang

Liu

et al. 2020

Sci Rep

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Enzymes as catalysts have attracted significant attention due to their excellent specificity and incomparable efficiency, but their practical application is limited because these catalysts are difficult to separate and recover. A magnetically recoverable biocatalyst has been effectively prepared through the immobilization of a nitroreductase (oxygen-insensitive, purified from Enterobacter cloacae) onto the fe 3 o 4 nanoparticles. the magnetic nanoparticles (Mnps) were synthesized by a coprecipitation method in an aqueous system. The surfaces of the MNPs were modified with sodium silicate and chloroacetic acid (CAA). Using 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) through a covalent binding, nitroreductase was loaded onto the modified magnetic carriers through covalent coupling, and thus, a magnetically recoverable biocatalyst was prepared. The free and immobilized nitroreductase activity was also investigated by the reduction of p-nitrobenzonitrile using nicotinamide adenine dinucleotide phosphate (NAPDH) as a cofactor. The activity of the immobilized enzyme was able to maintain 83.23% of that of the free enzyme. The prepared enzyme can easily reduce substituted nitrobenzene to substituted aniline at room temperature and atmospheric pressure, and the yield is up to 60.9%. Most importantly, the loaded nitroreductase carriers can be easily separated and recycled from the reaction system using an externally applied magnetic field. The magnetically recoverable biocatalyst can be recycled and reused 7 times while maintaining high activities and the activity of the magnetic catalyst can be maintained at more than 85.0% of that of the previous cycle. This research solves the recovery problem encountered in industrial applications of biocatalysts and presents a clean and green method of preparing substituted aniline.Biocatalysis is an important green and sustainable technology, because it is an ideal approach that can be used to meet the challenges of energy conservation and environmental sustainability 1,2 . Enzymes, which are natural biocatalysts, are becoming more and more important in industrial applications, because enzymes can be used at pH values, temperatures and pressures that are moderate, and enzymes form few byproducts and have high activities and an unparalleled selectivity 3-5 . However, there are two challenges that need to be addressed in practical applications. One of the challenges is that enzymes can be denatured, i.e., the native three-dimensional structure unfolds, and this occurs as a result of exposure of the enzyme to solvents or changes in the temperature and pH. Another challenge is that enzyme reuse is often hardly feasible. The recovery and reuse of enzymes is also a decisive factor in the production cost 6 .Specifically, enzymes lack long term stability under processing conditions, and it is very difficult to recover the enzyme from the reaction system. Most heterogeneous systems require either a filtration or centrifugation step or tedious processing of the final react...

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Imidazolium chloride-Co(iii) complex immobilized on Fe₃O₄@SiO₂ as a highly active bifunctional nanocatalyst for the copper-, phosphine-, and base-free Heck and Sonogashira reactions

Abstract: A green and efficient method has been developed for Heck and Sonogashira reactions by a magnetic Co(iii) bi-functional catalyst.

Cited by 53 publications

References 58 publications

Mg‐catalyzed one‐pot preparation of benzimidazoles and spirooxindoles by an immobilized chlorophyll b on magnetic nanoparticles

Mg‐catalyzed one‐pot preparation of benzimidazoles and spirooxindoles by an immobilized chlorophyll b on magnetic nanoparticles

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Reduction of nitroarenes by magnetically recoverable nitroreductase immobilized on Fe3O4 nanoparticles

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Imidazolium chloride-Co(iii) complex immobilized on Fe3O4@SiO2 as a highly active bifunctional nanocatalyst for the copper-, phosphine-, and base-free Heck and Sonogashira reactions

Abstract: A green and efficient method has been developed for Heck and Sonogashira reactions by a magnetic Co(iii) bi-functional catalyst.

Cited by 53 publications

References 58 publications

Mg‐catalyzed one‐pot preparation of benzimidazoles and spirooxindoles by an immobilized chlorophyll b on magnetic nanoparticles

Mg‐catalyzed one‐pot preparation of benzimidazoles and spirooxindoles by an immobilized chlorophyll b on magnetic nanoparticles

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Reduction of nitroarenes by magnetically recoverable nitroreductase immobilized on Fe3O4 nanoparticles

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Imidazolium chloride-Co(iii) complex immobilized on Fe₃O₄@SiO₂ as a highly active bifunctional nanocatalyst for the copper-, phosphine-, and base-free Heck and Sonogashira reactions