CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids

Alves, Diego; Santos, Cayane Genro; Paixão, Márcio W.; Soares, Letiére C.; Souza, Diego de; Rodrigues, Oscar E. D.; Braga, Antônio L.

doi:10.1016/j.tetlet.2009.09.052

Cited by 99 publications

(33 citation statements)

References 41 publications

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“…Copper(II) oxide nanoparticles ( NP CuO) are used as antimicrobial agents in textiles (Ren et al 2009) and paints (Cooney 1995), as catalysts in organic synthesis (Alves et al 2009), in the oxidation of pollutants (Moshe et al 2009), and they are also generated from electronics waste. Unfortunately, industrial use of NP CuO represents a potential health and environmental concern because the particles are toxic and mutagenic.…”

Section: Introductionmentioning

confidence: 99%

Reactive oxygen species generation by copper(II) oxide nanoparticles determined by DNA damage assays and EPR spectroscopy

et al. 2017

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Copper(II) oxide nanoparticles (NPCuO) have many industrial applications, but are highly cytotoxic because they generate reactive oxygen species (ROS). It is unknown whether the damaging ROS are generated primarily from copper leached from the nanoparticles, or whether the nanoparticle surface plays a significant role. To address this question, we separated nanoparticles from the supernatant containing dissolved copper, and measured their ability to damage plasmid DNA with addition of hydrogen peroxide, ascorbate, or both. While DNA damage from the supernatant (measured using an electrophoresis assay) can be explained solely by dissolved copper ions, damage by the nanoparticles in the presence of ascorbate is an order of magnitude higher than can be explained by dissolved copper and must therefore depend primarily upon the nanoparticle surface. DNA damage is time-dependent, with shorter incubation times resulting in higher EC50 values. Hydroxyl radical is the main ROS generated by NPCuO/hydrogen peroxide as determined by EPR measurements; NPCuO/hydrogen peroxide/ascorbate conditions generate ascorbyl, hydroxyl, and superoxide radicals. Thus, NPCuO generate ROS through several mechanisms, likely including Fenton-like and Haber-Weiss reactions from the surface or dissolved copper ions. The same radical species were observed when NPCuO suspensions were replaced with the supernatant containing leached copper, washed NPCuO, or dissolved copper solutions. Overall, NPCuO generate significantly more ROS and DNA damage in the presence of ascorbate than can be explained simply from dissolved copper, and the NPCuO surface must play a large role.

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Section: Introductionmentioning

confidence: 99%

Reactive oxygen species generation by copper(II) oxide nanoparticles determined by DNA damage assays and EPR spectroscopy

et al. 2017

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Section: Resultsmentioning

confidence: 99%

“…11, 2010 Moreover, CuO nanoparticles (NPs) have been employed as a mediator, as an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids (Scheme 3). 26 Generally, this kind of reaction involves particularly specific ligands which limiting the scope of potential applications.These ligand-free cross-coupling reactions of organic diselenides with aryl boronic acids using a catalytic amount of CuO nanoparticles in DMSO at 100 0 C under air atmosphere afford the corresponding products in good to excellent yields. The catalyst can be easily recovered and utilized for further catalytic reactions, as depicted in Figure 2.…”

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confidence: 99%

Transition metal oxide nanopowder and ionic liquid: an efficient system for the synthesis of diorganyl selenides, selenocysteine and derivatives

Narayanaperumal¹,

Gul²,

Kawasoko³

et al. 2010

J. Braz. Chem. Soc.

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Neste trabalho foi desenvolvido um método eficiente para a síntese de selenetos de diorganoíla e β-seleno aminas empregando Zn, quantidades catalíticas de ZnO nanoestruturado e líquidos iônicos (LI) como solventes recicláveis. Este sistema ZnO/LI apresentou alta eficiência nesta transformação, levando à formação dos produtos desejados em bons rendimentos.We have developed an efficient method for the synthesis of diorganyl selenides and β-seleno amines using Zn, catalytic amounts of ZnO nanopowder, as a catalyst and ionic liquid as a recyclable solvent. This ZnO/ionic liquid system shows high efficiency in catalyzing these transformations with the formation of the desired products in high yields. Keywords: synthesis, nanocatalysis, ionic liquids, selenium, selenocysteine, selenides IntroductionThe attention gained by organoselenides has been driven by the potential applications of selenium compounds in modern organic syntheses and asymmetric catalysis. 1,2 Their importance stems from the prevalence of C-Se bonds in compounds with biological and pharmaceutical impact, e.g., selenocarbo-hydrates, 3 selenoamino acids 4 and selenopeptides. 5 This class of molecules performs multiple therapeutic functions of great importance, for example, in antiviral to anticancer agents and in a variety of situations where free radicals are involved. 6 Organoselenium compounds are important synthetic intermediates, and the formation of symmetrical and unsymmetrical diorganyl selenides is an area of intense research. In general, diselenide bond cleavage is carried out employing common reducing agents and expensive metal sources, as depicted in Scheme 1. 7,8 Furthermore, reductive cleavage achieved by CsOH, 7 ArB(OH) 2 /CuI 8 and photochemical reactions 7 has been reported in a substantial number of previous studies.Reactions catalyzed by transition metal complexes have made a great contribution to the recent advances in relation to the cross-coupling reactions of diaryl diselenides with aryl halides. [9][10][11][12] However, most of the methods available to synthesize diorganyl selenides have serious disadvantages including: i) the use of expensive metal sources and J. Braz. Chem. Soc. 2080 reagents such as La, Yb, In, InI, and SmI 2, etc.; ii) handling difficulties; iii) functional group incompatibility; iv) difficult work-up procedures; v) harsh reaction conditions, such as the use of strong acids or bases and vi) high temperatures or long reaction times. Thus, there is still considerable interest in the development of highly efficient methods for this transformation. 13 Designing new specific catalysts and exploring their catalytic activity can have significant effects on optimizing the efficiency of a wide range of organic synthesis techniques, and has resulted in more economical and environmentally-friendly chemical processes through the replacement of nonselective, unstable or expensive catalysts.Nanotechnology is an emerging approach towards synthetic organic chemistry, particularly the area of nano-catalyzed organic tra...

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“…CuO nanoparticle-catalyzed coupling reactions of organic diselenides with aryl boronic acids to form organic selenides has been reported by Alves et al [90] This ligand-free coupling reaction involved the use of CuO nanoparticles (3 mol %), diphenyl diselenide (0.25 mmol), phenyl boronic acid (1.5 equiv), and DMSO as a solvent. The heterogeneous reaction mixture was stirred for 24 h at 100 8C under air to afford the corresponding diaryl selenide in high yields (Scheme 22).…”

Section: Cross-coupling Reactions Of Organic Diselenide With Aryl Bormentioning

confidence: 97%

Copper Nanoparticle‐Catalyzed CarbonCarbon and CarbonHeteroatom Bond Formation with a Greener Perspective

et al. 2011

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The carbon-carbon and carbon-heteroatom bond formations constitute the backbone of organic synthesis and have been widely used in the synthesis of natural products and useful compounds. Because of growing environmental concern, more attention has been focussed on the development of greener methods. Copper is environment-friendly and comparatively inexpensive. Although the use of copper salts in catalysis has been known since the last century, this area of research has been less explored compared to other metals, such as palladium, magnesium, and zinc. This review highlights the general features of nanoparticles as catalysts with particular reference to copper and the recent developments in the copper(0) nanoparticle-catalyzed C(aryl)-C(aryl/alkynyl), C(aryl)-N, C(aryl)-O, C(aryl)-S, and C(aryl)-Se bond formations and related reactions. The mechanisms of the reactions have been outlined and discussed with respect to the active catalytic species and possible intermediates. The scope, limitations, and green aspects of the reactions have also been highlighted. The convenient methods of preparation of copper nanoparticles and their characterization are described.

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CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids

Cited by 99 publications

References 41 publications

Reactive oxygen species generation by copper(II) oxide nanoparticles determined by DNA damage assays and EPR spectroscopy

Reactive oxygen species generation by copper(II) oxide nanoparticles determined by DNA damage assays and EPR spectroscopy

Transition metal oxide nanopowder and ionic liquid: an efficient system for the synthesis of diorganyl selenides, selenocysteine and derivatives

Copper Nanoparticle‐Catalyzed CarbonCarbon and CarbonHeteroatom Bond Formation with a Greener Perspective

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