Coordinated copper(II) supported on silica nanospheres applied to the synthesis of α-ketoamides via oxidative amidation of methyl ketones

Sharma, Rakesh Kumar; Sharma, Shivani; Gaba, Garima; Dutta, Sriparna

doi:10.1007/s10853-015-9522-y

Cited by 10 publications

(11 citation statements)

References 66 publications

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“…In a significant improvement Liu and co-workers 78 reported a room-temperature copper-catalyzed aerobic oxidation for the synthesis of α-ketoamides from arylmethyl ketones in the Along the same line, a copper-catalyzed aerobic oxidative coupling of aryl methyl ketones with N,N-dimethylformamide was reported by Zhou and Song 82 to afford α-ketoamides by sequential dioxygen activation, C−H bond functionalization, and amide bond formation. In 2016, Dutta and co-workers 83 reported the oxidative amidation of methyl ketones to αketoamides using hydrogen peroxide as the stoichiometric oxidant and iodine as an additive under mild reaction conditions in the presence of a heterogeneous retrievable silica nanosphere supported copper catalytic system (SiO 2 @ APTES@DAP-Cu). This catalyst was prepared via immobilization of diacetylpyridine (DAP) onto amine-functionalized silica nanospheres (Figure 6).…”

Section: α-Ketoamide Syntheses Under Copper Catalysismentioning

confidence: 99%

Recent Advances in the Catalytic Synthesis of α-Ketoamides

2016

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α-Ketoamides and their derivatives are key constituents of natural products, biologically relevant molecules, drug and drug candidates, and functional materials. Further, they are versatile and valuable intermediates and synthons in a number of functional group transformations and total syntheses. In recent years tremendous growth has been realized in the development of synthetic methods for α-ketoamide preparation and their applications in synthetic and medicinal chemistry. Among the various catalytic methods of α-ketoamide formation, two approaches, namely double aminocarbonylation and oxidative amidation, have received much more attention and have been greatly studied because of the ready availability of the starting materials, use of carbon monoxide (CO) as a direct source of carbonyl functionalities, and use of molecular oxygen (O2) or air as a green terminal oxidant and/or reactants. Catalyzed α-ketoamide formation can be roughly classified into metal- and nonmetal-catalyzed processes. In the context of metal catalysis, most reactions involving metals are performed using palladium (Pd) and copper (Cu); however, other metals such as gold (Au), silver (Ag), and iron (Fe) based catalysts have also been investigated to some extent. On the other hand, nonmetal-catalyzed α-ketoamide syntheses are mainly restricted to iodine-based catalysts in the presence or absence of other promoters. Our objective in this review is to highlight the important research endeavors related to catalytic α-ketoamide synthesis, which include the trends in the catalytic synthesis of α-ketoamides, new breakthroughs, and recent advances up to March 2016.

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Section: α-Ketoamide Syntheses Under Copper Catalysismentioning

confidence: 99%

Recent Advances in the Catalytic Synthesis of α-Ketoamides

2016

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“…Magnetic nanoparticles (MNPs) as a solid support material have been widely utilized for the design of heterogeneous catalysts in many MCRs . Other important features of these magnetic catalysts are high stability, low toxicity, easy synthesis and high catalytic activities.…”

Section: Introductionmentioning

confidence: 99%

H₃PMo₁₂O₄₀‐immobilized chitosan/Co₃O₄: A novel and recyclable nanocomposite for the synthesis of pyrimidinedione derivatives

Safari

Tavakoli

Ghasemzadeh

2019

Applied Organom Chemis

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An efficient three‐component reaction of aromatic aldehydes, 6‐aminouracil/6‐amino‐1,3‐dimethyluracil and 4‐hydroxycoumarin in the presence of a novel heterogeneous catalyst H3PMo12O40‐immobilized Co3O4/chitosan led to a synthesis of a new class of pyrimidinedione derivatives under reflux conditions. The magnetically recoverable nanocomposite of Co3O4/chitosan/H3PMo12O40 was fully characterized by Fourier transform‐infrared spectrophotometry, scanning electron microscopy, X‐ray powder diffraction, energy‐dispersive X‐ray spectroscopy, vibrating‐sample magnetometry and N2 adsorption–desorption by Brunauer–Emmett–Teller analysis. Results show that Keggin‐type 12‐molybdophosphoric acid immobilized into the network of the cross‐linked chitosan with super‐paramagnetic Co3O4 nanoparticles. The present method offers several advantages, such as simple procedure, short reaction times and excellent yields of products. The novelty of the catalyst, high catalytic activity, easy separation from the reaction with an external magnetic field and reusability of the catalyst in six consecutive runs are additional eco‐friendly attributes of this catalytic system.

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“…There are different types of solid support e. g . polymer,, zeolite, alumina, silica, graphene, mesoporous carbon, carbon nanotube, metal‐organic framework,, metal oxide nanoparticles, etc ,. Use of mesoporous silica as solid support adds few advantages.…”

Section: Introductionmentioning

confidence: 99%

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

et al. 2017

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Mesoporous silica has been functionalized with 3‐aminopropyl triethoxy silane (3‐APTES), followed by Schiff‐base condensation with 2‐hydroxy‐1‐naphthaldehyde. Incorporation of copper and nickel by covalent grafting onto the Schiff‐base loaded materials gives two heterogenized catalysts namely, Cu–Cat and Ni‐Cat, respectively. The materials have been characterized by PXRD analyses, nitrogen sorption studies, TEM, TGA, FT‐IR, UV‐visible and solid state MAS‐NMR spectroscopy. The metal‐contents in the samples are estimated using ICP‐AES studies. Cu–Cat and Ni‐Cat have been used as active catalyst in the oxidation of various olefins e. g. styrene, α‐methyl styrene, cyclohexene, trans stilbene and cyclooctene in the presence of tert‐butyl hydroperoxide as the oxidant in acetonitrile under mild conditions. Different products have been analyzed by gas chromatography and gas chromatography‐mass spectrometry. The results show high conversion of the substrates, moderate to good product selectivity and high TOFs of the reactions. The catalysts are recycled without deteriorating their activities and heterogeneous nature.

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Coordinated copper(II) supported on silica nanospheres applied to the synthesis of α-ketoamides via oxidative amidation of methyl ketones

Cited by 10 publications

References 66 publications

Recent Advances in the Catalytic Synthesis of α-Ketoamides

Recent Advances in the Catalytic Synthesis of α-Ketoamides

H₃PMo₁₂O₄₀‐immobilized chitosan/Co₃O₄: A novel and recyclable nanocomposite for the synthesis of pyrimidinedione derivatives

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

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Coordinated copper(II) supported on silica nanospheres applied to the synthesis of α-ketoamides via oxidative amidation of methyl ketones

Cited by 10 publications

References 66 publications

Recent Advances in the Catalytic Synthesis of α-Ketoamides

Recent Advances in the Catalytic Synthesis of α-Ketoamides

H3PMo12O40‐immobilized chitosan/Co3O4: A novel and recyclable nanocomposite for the synthesis of pyrimidinedione derivatives

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

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H₃PMo₁₂O₄₀‐immobilized chitosan/Co₃O₄: A novel and recyclable nanocomposite for the synthesis of pyrimidinedione derivatives