C-Arylation reactions catalyzed by CuO-nanoparticles under ligand free conditions

Kidwai, Mazaahir; Bhardwaj, Shweta; Poddar, Roona

doi:10.3762/bjoc.6.35

Cited by 29 publications

(27 citation statements)

References 35 publications

(31 reference statements)

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“…18,19 However, up to now nanoscale copper(I) catalysed cross coupling reactions, especially C-N bond formation, have rarely been reported in scientific literature 13,[20][21][22] or show drawbacks in versatility and catalyst loadings. 20,[22][23][24][25] Furthermore, it would be more convenient to conduct catalysis at temperatures right below the boiling point of water without the necessity for ligands, additives and inert reaction conditions. 26 Nonetheless, we want to establish a Cu 2 Onanocatalyst which combines the advantages of classical homogeneous and heterogeneous catalyses.…”

Section: Introductionmentioning

confidence: 99%

Ligand-free copper(i) oxide nanoparticle-catalysed amination of aryl halides in ionic liquids

Kessler

Robke

Sahler

et al. 2014

Catal. Sci. Technol.

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In the following, we present a simple and feasible methodology for a C-N coupling reaction using nanoscale Cu 2 O catalysts incorporated in n-Bu 4 POAc ionic liquid media. It is shown that a wide range of amines and aryl halides can be coupled selectively in high yields, without the use of ligands or additives (bases) and without precautions against water or air. All catalyses can be carried out with a nanoparticle catalyst loading as low as 5 mol%, based on the used precursor.

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Section: Introductionmentioning

confidence: 99%

Ligand-free copper(i) oxide nanoparticle-catalysed amination of aryl halides in ionic liquids

Kessler

Robke

Sahler

et al. 2014

Catal. Sci. Technol.

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“…[53] Almost at the same time, Ma and co-workers developed the synthesis of similar indole products by using N-COCF 3 -protected ohaloanilines (33) and 1,3-dicarbonyl compounds. 1 1 2 2 3 3 4 4 5 5 6 6 7 7 8 8 9 9 10 10 11 11 12 12 13 13 14 14 15 15 16 16 17 17 18 18 19 19 20 20 21 21 22 22 23 23 24 24 25 25 26 26 27 27 28 28 29 29 30 30 31 31 32 32 33 33 34 34 35 35 36 36 37 37 38 38 39 39 40 40 41 41 42 42 43 43 44 44 45 45 46 46 47 47 48 48 49 49 50 50 51 51 52 52 53 53 54 54 55 55 56 56 57 57 philic addition of the active acarbon atom to the COCF 3 carbonyl group in compound 36, 2trifluoromethyl indoles (39) were formed through a cascade sequence from intermediates 37 and 39 (Scheme 25). However, accessing the indole products involved further hydrolysis (Scheme 23).…”

Section: Initiated Tandem Reactions For the Synthesis Of Cyclic And Hmentioning

confidence: 99%

“…1 1 2 2 3 3 4 4 5 5 6 6 7 7 8 8 9 9 10 10 11 11 12 12 13 13 14 14 15 15 16 16 17 17 18 18 19 19 20 20 21 21 22 22 23 23 24 24 25 25 26 26 27 27 28 28 29 29 30 30 31 31 32 32 33 33 34 34 35 35 36 36 37 37 38 38 39 39 40 40 41 41 42 42 43 43 44 44 45 45 46 46 47 47 48 48 49 49 50 50 51 51 52 52 53 53 54 54 55 55 56 56 57 57 conditions. [39] According to the work of Langer and co-workers, a-aryl dicarbonyl compounds, which were readily synthesized from these coupling reactions, were useful starting materials for the synthesis of biaryl compounds (5; Scheme 12). [37] On the other hand, biimidazole ligand L7 was effective in facilitating the coupling reaction between diketones and aryl iodides/bromides.…”

Section: Introductionmentioning

confidence: 99%

Advances in Copper‐Catalyzed CC Coupling Reactions and Related Domino Reactions Based on Active Methylene Compounds

Liu

Wan

2012

Chemistry An Asian Journal

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Active methylene compounds are a major class of reaction partners for C-C bond formation with sp(2) C-X (X = halide) fragments. As one of the most-classical versions of the Ullmann-type coupling reaction, activated-methylene-based C-C coupling reactions have been efficiently employed in a large number of syntheses. Although this type of reaction has long relied on noble-metal catalysis, the renaissance of copper catalysis at the end of last century has led to dramatic developments in Ullmann C-C coupling reactions. Owing to its low cost, abundance, as well as excellent catalytic activity, the exceptional atom economy of copper catalysis is gaining widespread attention in various organic synthesis. This review summarizes the advances in copper-catalyzed intermolecular and intramolecular C-C coupling reactions that use activated methylene species as well as in tandem reactions that are initiated by this transformation.

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“…[44] C-Arylation of acetylacetone and dimethyl malonate with a variety of substituted iodobenzenes provided the corresponding products in high yields.…”

Section: Arylation Of Active Methylene Compoundsmentioning

confidence: 99%

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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C-Arylation reactions catalyzed by CuO-nanoparticles under ligand free conditions

Cited by 29 publications

References 35 publications

Ligand-free copper(i) oxide nanoparticle-catalysed amination of aryl halides in ionic liquids

Ligand-free copper(i) oxide nanoparticle-catalysed amination of aryl halides in ionic liquids

Advances in Copper‐Catalyzed CC Coupling Reactions and Related Domino Reactions Based on Active Methylene Compounds

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

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