(Thio)urea containing quaternary ammonium salts for the CO2-fixation with epoxides

Schörgenhumer, Johannes; Tiffner, Maximilian; Waser, Mario

doi:10.1007/s00706-019-02391-w

Cited by 13 publications

(14 citation statements)

References 41 publications

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“…The catalytic activity of the N‐DFNS‐700/TBAI system was further compared with recently reported catalysts and it was observed that the N‐DFNS showed comparable activity at mild reaction conditions (Table 2). [16–31] …”

Section: Resultsmentioning

confidence: 99%

Nitridated Fibrous Silica/Tetrabutylammonium Iodide (N‐DFNS/TBAI): Robust and Efficient Catalytic System for Chemical Fixation of Carbon Dioxide to Cyclic Carbonates

et al. 2021

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The development of an active and competent catalyst for the conversion of carbon dioxide (CO2) to value added‐chemicals at low pressure and temperature have great importance in the field of industrial chemical production as well as in tackling global warming. In this report, nitridated dendritic fibrous nano‐silica (N‐DFNS) as highly porous and stable nano‐material have been synthesized by using ammonolysis reaction at various temperature ranging from 500–800 °C and used as heterogeneous catalysts in combination with TBAI for the synthesis of cyclic carbonates from CO2 and epoxide. The presence of high surface area balanced acid‐base bi‐functionalities generated on silica due to ammonolysis offered high activity towards the synthesis of cyclic carbonates at the atmospheric pressure with excellent recyclability.

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Section: Resultsmentioning

confidence: 99%

Nitridated Fibrous Silica/Tetrabutylammonium Iodide (N‐DFNS/TBAI): Robust and Efficient Catalytic System for Chemical Fixation of Carbon Dioxide to Cyclic Carbonates

et al. 2021

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“…During the whole process, thiourea not only activated hydrogen bonds but also promoted the conversion of carbon dioxide, playing a synergistic role with the adjacent quaternary ammonium salt components to ensure the coupling reaction proceed smoothly. It should be mentioned that other possible mechanisms like thiourea catalyst as a nucleophile also have been proposed …”

Section: Resultsmentioning

confidence: 99%

“…Diallyl‐dibutyl‐ammonium bromide ( N m1 ), triallyl‐butyl‐ammonium bromide ( N m2 ), tetraallyl‐ammonium bromide ( N m3 ), and N, N′‐diallylthiourea ( L m1 ) were prepared according to the literature and more detail were provided in Figure S1. Pentaerythritol tetrakis (3‐mercaptopropionate) ( C m3 ), diphenyl (2,4,6‐trimethylbenzoyl) phosphine oxide (TPO) and all epoxides were purchased from Sun Chemical Technology Co., Ltd.…”

Section: Methodsmentioning

confidence: 99%

Crosslinked Resin‐Supported Bifunctional Organocatalyst for Conversion of CO₂ into Cyclic Carbonates

et al. 2020

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The development of solvent‐free, metal‐free, recyclable organic catalysts is required for the current chemical fixation of carbon dioxide converted into cyclic carbonates. With the goal of reducing the cost, time, and energy consumption for the coupling reaction of CO2 and epoxides, a series of highly active heterogeneous catalysts, based on a thiourea and quaternary ammonium salt system, are synthesized by using a thiol‐ene click reaction under ultraviolet light. Benefitting from synergistic interactions of the electrophilic center (thiourea) and the nucleophilic site (ammonium bromide), the catalysts exhibit excellent catalytic selectivity (99 %) for the cycloaddition of carbon dioxide with a diverse range of epoxides under mild conditions (1.2 MPa, 100 °C). Moreover, the catalyst can be easily recycled by facile filtration and reused for 5 times without noticeable loss of activity and selectivity. This work provides a potential heterogeneous catalyst for the conversion of carbon dioxide into high value‐added chemicals with the combined advantages of low cost, easy recovery, and satisfactory catalytic properties.

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“…32 The urea moiety on the ammonium bromide catalyst functions as a hydrogen-bonding donor to activate epoxide substrates. 33,34 An optimized bifunctional ammonium bromide catalyst could efficiently promote the reaction of glycidyl ethers and aryl isocyanates to provide corresponding 2-oxazolidinone products 1 in good to high yields.…”

Section: Bifunctional Organocatalystsmentioning

confidence: 99%

Efficient methods for the synthesis of chiral 2‐oxazolidinones as pharmaceutical building blocks

et al. 2022

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Although the wide variety of heterocyclic compounds is common knowledge, chiral 2‐oxazolidinones are recognized as some of the most important heterocycles in medicinal chemistry. Many important pharmaceutical molecules have been constructed based on the chiral 2‐oxazolidinone backbone. Therefore, the development of even more efficient catalytic methods for the synthesis of chiral 2‐oxazolidinones remains a very important pursuit in the field of synthetic organic chemistry. This review summarizes the coupling reactions of epoxides and isocyanates for the preparation of 2‐oxazolidinones. Both metal catalysts and organocatalysts promote these reactions. Optically pure 2‐oxazolidinones are prepared from optically pure epoxide substrates via these catalytic methods. A synthetic example of a commercially available pharmaceutical compound utilizing this method is also introduced.

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(Thio)urea containing quaternary ammonium salts for the CO2-fixation with epoxides

Cited by 13 publications

References 41 publications

Nitridated Fibrous Silica/Tetrabutylammonium Iodide (N‐DFNS/TBAI): Robust and Efficient Catalytic System for Chemical Fixation of Carbon Dioxide to Cyclic Carbonates

Nitridated Fibrous Silica/Tetrabutylammonium Iodide (N‐DFNS/TBAI): Robust and Efficient Catalytic System for Chemical Fixation of Carbon Dioxide to Cyclic Carbonates

Crosslinked Resin‐Supported Bifunctional Organocatalyst for Conversion of CO₂ into Cyclic Carbonates

Efficient methods for the synthesis of chiral 2‐oxazolidinones as pharmaceutical building blocks

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(Thio)urea containing quaternary ammonium salts for the CO2-fixation with epoxides

Cited by 13 publications

References 41 publications

Nitridated Fibrous Silica/Tetrabutylammonium Iodide (N‐DFNS/TBAI): Robust and Efficient Catalytic System for Chemical Fixation of Carbon Dioxide to Cyclic Carbonates

Nitridated Fibrous Silica/Tetrabutylammonium Iodide (N‐DFNS/TBAI): Robust and Efficient Catalytic System for Chemical Fixation of Carbon Dioxide to Cyclic Carbonates

Crosslinked Resin‐Supported Bifunctional Organocatalyst for Conversion of CO2 into Cyclic Carbonates

Efficient methods for the synthesis of chiral 2‐oxazolidinones as pharmaceutical building blocks

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Crosslinked Resin‐Supported Bifunctional Organocatalyst for Conversion of CO₂ into Cyclic Carbonates