A green and efficient Pd-free protocol for the Suzuki–Miyaura cross-coupling reaction using Fe3O4@APTMS@Cp2ZrClx(x = 0, 1, 2) MNPs in PEG-400

Zeynizadeh, Behzad; Mousavi, Hossein; Sepehraddin, Farhad

doi:10.1007/s11164-020-04145-4

Cited by 18 publications

(6 citation statements)

References 135 publications

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“…Among different solvents such as PEG‐400, n‐hexane, toluene, DMF, DMSO, H 2 O, and EtOH, it turned out that PEG‐400 as a green solvent gives excellent conversion compared with other polar/nonpolar solvents. Over and above that, PEG‐400 has fascinating applications such as reduction, 74 oxidation, 75 substitution, 76 and coupling 77 . The activity of Pd 2 ‐Cu 3 @MX/CNT has also boosted under sonication, and the reaction time is reduced compared with a high‐speed stirrer.…”

Section: Resultsmentioning

confidence: 99%

“…Over and above that, PEG-400 has fascinating applications such as reduction, 74 oxidation, 75 substitution, 76 and coupling. 77 The activity of Pd 2 -Cu 3 @MX/CNT has also boosted under sonication, and the reaction time is reduced compared with a high-speed stirrer. Furthermore, increasing the power from 60 to 90 W has not significantly affected time reaction or reaction conversion.…”

Section: Synthesis Of 23-dihydro Quinazoline-4(1h)-onesmentioning

confidence: 99%

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Stabilization and anchoring of palladium‐copper alloy on murexide modified carbon nanotube as a superb nanocatalyst: Excellent performance in coupling and synthetic reactions

Mohammadlou,

Noroozi Pesyan

2023

Applied Organom Chemis

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Sketching a proper catalytic system with supplementary attributes, containing easy separation, wide surface area, supreme loading capacity, and fantastical electronic attributes, proposes an encouraging direction for efficiently using nanostructures for various applications. However, the capability to adjust the nano‐measure bimetallic particles is an adjustment for attaining superb performance in the catalytic field. Herein, an environmentally benign approach was developed for immobilizing and anchoring Pd‐Cu alloy nanoparticles on murexide (MX)‐functionalized carbon nanotubes (CNTs). Afterward, the catalytic activity of Pd2‐Cu3@MX/CNT was studied in synthesizing 2,3‐dihydro quinazoline‐4(1H)‐ones and carbon–carbon coupling reactions at sustainable reaction conditions under ultrasound irradiation. The results demonstrated that high‐affinity MX ligand and porous CNT structures than the adsorption of Pd–Cu had a unique designation in the high‐range constancy of the alloy nanoparticles and following catalytic activity. In addition, ultrasound irradiation got electrons of Pd–Cu alloy nanoparticles agitated, constructing a synergic efficacy between Cu and Pd metals for synthesis and coupling reactions. Our study represents that the designed catalyst is green, recyclable, and most suitable, providing new intuition into in high‐range constancy of bimetallic nanoparticles for broad applications.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of 23-dihydro Quinazoline-4(1h)-onesmentioning

confidence: 99%

Stabilization and anchoring of palladium‐copper alloy on murexide modified carbon nanotube as a superb nanocatalyst: Excellent performance in coupling and synthetic reactions

Mohammadlou,

Noroozi Pesyan

2023

Applied Organom Chemis

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“…Furthermore, the TON and TOF values were obtained up to 481 and 2884, respectively, for the mentioned Suzuki-Miyaura cross-coupling reaction. Zeynizadeh and co-workers recently reported the use of PEG-400 as a green solvent for a Pd-free catalytic system in the Suzuki-Miyaura cross-coupling reaction [69]. A robust magnetic and reusable catalyst, Fe 3 O 4 @APTMS@Cp 2 ZrCl x(x = 0,1,2) magnetic nanoparticles (MNPs) (APTMS: (3-aminopropyl)trimethoxysilane), presenting a core shell structure and previously prepared by the authors, was used in this system.…”

Section: Poly(ethylene Glycol)mentioning

confidence: 99%

“…Suzuki-Miyaura cross-coupling reaction in the presence of Fe3O4@APTMS@Cp2ZrClx(x = 0, 1, 2) as a Pd-free nanocatalyst in PEG-400[69]. APTMS: (3-aminopropyl)trimethoxysilane.…”

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confidence: 99%

New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions

Andrade

Martins

2020

Molecules

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The ever-growing interest in the cross-coupling reaction and its applications has increased exponentially in the last decade, owing to its efficiency and effectiveness. Transition metal-mediated cross-couplings reactions, such as Suzuki–Miyaura, Sonogashira, Heck, and others, are powerful tools for carbon–carbon bond formations and have become truly fundamental routes in catalysis, among other fields. Various greener strategies have emerged in recent years, given the widespread popularity of these important reactions. The present review comprises literature from 2015 onward covering the implementation of unconventional methodologies in carbon–carbon (C–C) cross-coupling reactions that embodies a variety of strategies, from the use of alternative energy sources to solvent- free and green media protocols.

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“…This contributes significantly to the efficient production of a wide range of therapeutic agents. Notable examples of pharmaceuticals synthesized using the Suzuki-Miyaura reaction include ruxolitinib, rucaparib, fluxapyroxad, losartan, etoricoxib, lapatinib, and pyridovericin, 2,3 as shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Modified electrodes: Utilizing Cu‐modified graphene oxide nanosheets as a cathode in electro‐oxidation synthesis of mild Suzuki–Miyaura cross‐coupling reaction under green and sustainable conditions

Abdullaev,

Singh,

Al‐Delfi

et al. 2024

Applied Organom Chemis

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This study presents an eco‐conscious approach to enhance the efficiency of the Suzuki–Miyaura cross‐coupling reaction. We first synthesized graphene oxide nanosheets using the Hummers method and then coated them to incorporate metallic copper on their surface. Following this, we conducted various analyses, including Fourier transform infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), Brunauer–Emmett–Teller (BET) analysis, cyclic voltammetry (CV), and energy‐dispersive X‐ray spectroscopy (EDS) identification, to characterize these modified nanosheets. Subsequently, we utilized Cu‐modified graphene oxide nanosheets as cathode catalysts in an electro‐oxidation synthesis setup. To verify the effectiveness of this novel approach, we utilized bromobenzene and phenylboronic acid as model substrates to synthesize biphenyl compounds. The reaction yielded impressive product yields ranging from 87% to 93%. Operating under environmentally friendly conditions, this electro‐oxidation synthesis not only enhances selectivity but also significantly reduces the environmental impact of the reaction. Our findings highlight the potential of this green chemistry strategy, offering a promising avenue for sustainable and efficient organic synthesis, as evidenced by the successful coupling of bromobenzene and phenylboronic acid with consistently high yields.

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A green and efficient Pd-free protocol for the Suzuki–Miyaura cross-coupling reaction using Fe3O4@APTMS@Cp2ZrClx(x = 0, 1, 2) MNPs in PEG-400

Cited by 18 publications

References 135 publications

Stabilization and anchoring of palladium‐copper alloy on murexide modified carbon nanotube as a superb nanocatalyst: Excellent performance in coupling and synthetic reactions

Stabilization and anchoring of palladium‐copper alloy on murexide modified carbon nanotube as a superb nanocatalyst: Excellent performance in coupling and synthetic reactions

New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions

Modified electrodes: Utilizing Cu‐modified graphene oxide nanosheets as a cathode in electro‐oxidation synthesis of mild Suzuki–Miyaura cross‐coupling reaction under green and sustainable conditions

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