KCC‐1 Supported Cu(II)‐β‐Cyclodextrin Complex as a Reusable Catalyst for the Synthesis of 3‐Aryl‐2‐oxazolidinones from Carbon Dioxide, Epoxide, Anilines

Sadeghzadeh, Seyed Mohsen; Zhiani, Rahele; Moradi, Marjan

doi:10.1002/slct.201800017

Cited by 27 publications

(21 citation statements)

References 41 publications

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“…Although three‐component reaction of amines, CO 2 and epoxides also produces oxazolidinones, low to no activities of aliphatic amines is a common limitation of this method ( vide supra ) –. It is thus important to study the performance of rare‐earth metal amides in catalyzing reaction of aliphatic amines, epoxides, and DMC.…”

Section: Resultsmentioning

confidence: 96%

A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare‐Earth Metal Amides

et al. 2019

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Three-component reaction of epoxides, amines, and dimethyl carbonate catalyzed by rare-earth metal amides has been developed to synthesize oxazolidinones. 47 examples of 3,5disubstituted oxazolidinones were prepared in 13-97 % yields. This is a simple and most practical method which employs easily available substrates and catalysts, and is applicable to a wide range of aromatic and aliphatic amines, as well as monosubstituted epoxides. Scope of disubstituted epoxides is rather limited, which requires further study. Preliminary mechanistic study reveals two possible reaction pathways through intermediates of β-amino alcohols or amides. using ethyl acetate/petroleum ether = 1/3-1/0, and the resulting oxazolidinone was characterized by 1 H and 13 C NMR spectroscopy and HR MS.

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Section: Resultsmentioning

confidence: 96%

A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare‐Earth Metal Amides

et al. 2019

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“…KCC-1 nanoparticles have been already encountered in this review in Table 4, entry 9. On this fibrous material was supported Cu (II)-β-cyclodextrin and the obtained catalyst afforded oxazolidinones from reaction of anilines, CO 2 and ethylene oxide (Scheme 21, Equation (4)) [175]. Albeit restricted only to ethylene oxide and p-substituted anilines, this reaction is interesting because it did not use epoxide excess.…”

Section: Scheme 13mentioning

confidence: 99%

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

et al. 2019

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Carbon dioxide produced by human activities is one of the main contributions responsible for the greenhouse effect, which is modifying the Earth’s climate. Therefore, post-combustion CO2 capture and its conversion into high value-added chemicals are integral parts of today’s green industry. On the other hand, carbon dioxide is a ubiquitous, cheap, abundant, non-toxic, non-flammable and renewable C1 source. Among CO2 usages, this review aims to summarize and discuss the advances in the reaction of CO2, in the synthesis of cyclic carbonates, carbamates, and ureas appeared in the literature since 2017.

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“…Copper(II) forms a complex with CD in alkaline solution, and the complexes with α- and β-CD have already been isolated and characterized [58]. The efficacy of β-CD to direct and bind Cu when CD is bonded to silica has been already studied, and its catalytic activity as a Lewis acid has been demonstrated [59]. As the literature has focused mainly on the non-covalent bonding of β-CD onto the silica surface [60,61], we have aimed to explore the efficacy of β-CD that is covalently grafted onto silica to chelate Cu(II) and to exploit this system as a catalyst for alkyne-azide cycloaddition (CuAAC) in the absence of a reducing agent.…”

Section: Resultsmentioning

confidence: 99%

Sonochemically-Promoted Preparation of Silica-Anchored Cyclodextrin Derivatives for Efficient Copper Catalysis

et al. 2019

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Silica-supported metallic species have emerged as valuable green-chemistry catalysts because their high efficiency enables a wide range of applications, even at industrial scales. As a consequence, the preparation of these systems needs to be finely controlled in order to achieve the desired activity. The present work presents a detailed investigation of an ultrasound-promoted synthetic protocol for the grafting of β-cyclodextrin (β-CD) onto silica. Truly, ultrasound irradiation has emerged as a fast technique for promoting efficient derivatization of a silica surface with organic moieties at low temperature. Three different β-CD silica-grafted derivatives have been obtained, and the ability of β-CD to direct and bind Cu when CD is bonded to silica has been studied. A detailed characterization has been performed using TGA, phenolphthalein titration, FT-IR, diffuse reflectance (DR), DR UV-Vis, as well as the inductively-coupled plasma (ICP) of the β-CD silica-grafted systems and the relative Cu-supported catalysts. Spectroscopic characterization monitored the different steps of the reaction, highlighting qualitative differences in the properties of amino-derivatized precursors and final products. In order to ensure that the Cu-β-CD silica catalyst is efficient and robust, its applicability in Cu(II)-catalyzed alkyne azide reactions in the absence of a reducing agent has been explored. The presence of β-CD and an amino spacer has been shown to be crucial for the reactivity of Cu(II), when supported.

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KCC‐1 Supported Cu(II)‐β‐Cyclodextrin Complex as a Reusable Catalyst for the Synthesis of 3‐Aryl‐2‐oxazolidinones from Carbon Dioxide, Epoxide, Anilines

Cited by 27 publications

References 41 publications

A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare‐Earth Metal Amides

A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare‐Earth Metal Amides

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

Sonochemically-Promoted Preparation of Silica-Anchored Cyclodextrin Derivatives for Efficient Copper Catalysis

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