The reaction mechanism of incorporation of carbon dioxide into o-alkynylaniline derivatives catalyzed by silver salt

Ruan, Chengyan; Yang, Longhua; Yuan, Yuan; Yan, Jun; Wang, Hongming

doi:10.1016/j.comptc.2015.02.001

Cited by 12 publications

(5 citation statements)

References 34 publications

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“…Moreover, 2-oxazolidone heterocyclic compounds are a class of N-substituted five-membered cyclic carbonates with a structure very similar to that of 2-methylbut-3-yn-2-ol, which are also important intermediates for the production of drugs and fine chemicals. The catalytic performance of the Ag/Aza-COF in the reaction of propargylamine with CO 2 was also investigated. ,, As shown in Table , after 9 h of reaction, the reaction of 2-methylbut-3-yn-2-amine with CO 2 also reached 100% (entry 2f, Table ). The experiments confirm that the constructed Ag/Aza-COF possesses high efficiency on the cyclization of propargylamine and CO 2 .…”

Section: Resultsmentioning

confidence: 99%

“…The catalytic performance of the Ag/Aza-COF in the reaction of propargylamine with CO 2 was also investigated. 12,13,36 As shown in Table 2, after 9 h of reaction, the reaction of 2-methylbut-3-yn-2-amine with CO 2 also reached 100% (entry 2f, Table 2). The experiments confirm that the constructed Ag/Aza-COF possesses high efficiency on the cyclization of propargylamine and CO 2 .…”

Section: Co 2 Catalytic Conversionmentioning

confidence: 97%

“…In the last few decades, although many catalysts have been fabricated for CO 2 catalytic chemical conversion 3−13 and various chemicals have been produced with CO 2 as a carbon source, such as carbon monoxide (CO), 14,15 methane (CH 4 ), 16,17 formaldehyde (HCHO), 18−20 formic acid (HCOOH), 21,22 methanol (CH 3 OH), 23−25 ethanol (C 2 H 5 OH), 26−29 and other hydrocarbons, 30−35 the efficient conversion of CO 2 into high valueadded chemicals under mild conditions is still of significant challenge. 36 Among diverse heterogeneous catalysts, metal nanoparticles have become a group of promising efficient catalysts because they usually display high catalytic activity. 37 These metal nanoparticles usually have high surface energies.…”

Section: Introductionmentioning

confidence: 99%

“…Comparing with conventional C1 sources, such as carbon monoxide (CO) and phosgene, the stable electronic structure in CO 2 and the thermodynamic stability of CO (bond enthalpy 805 kJ/mol) in CO 2 result in a lower reactivity, which calls for a high driving force to ensure its efficient transformation. In the last few decades, although many catalysts have been fabricated for CO 2 catalytic chemical conversion – and various chemicals have been produced with CO 2 as a carbon source, such as carbon monoxide (CO), , methane (CH 4 ), , formaldehyde (HCHO), – formic acid (HCOOH), , methanol (CH 3 OH), – ethanol (C 2 H 5 OH), – and other hydrocarbons, – the efficient conversion of CO 2 into high value-added chemicals under mild conditions is still of significant challenge …”

Section: Introductionmentioning

confidence: 99%

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Effective CO₂ Catalytic Conversion by Nitrogen-Rich Covalent Organic Framework-Immobilized Ag Nanoparticles

Li,

Deng,

Wang

et al. 2023

ACS Appl. Nano Mater.

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Taking carbon dioxide (CO 2 ) as a significant C1 source and converting it into value-added chemicals presents a promising strategy for addressing the energy and environmental issues arising from excessive anthropogenic emissions. Nevertheless, catalytic CO 2 conversion, particularly under moderate conditions, remains a formidable challenge. Herein, a composite of Aza-COF-immobilized silver nanoparticles (Ag NPs), Ag/Aza-COF, was successfully fabricated by taking the nitrogen-rich COF, Aza-COF, as the porous carrier. Catalytic experiments revealed that with the presence of Ag/Aza-COF, 100% conversion of 2-methylbut-3-yn-2-ol to the corresponding alkylene cyclic carbonate was achieved after 9 h of reaction at ambient temperature and pressure using CH 3 CN as the solvent. Further studies revealed that the Ag/Aza-COF exhibits very high catalytic activity and effective recyclability in CO 2 fixation with alkynyl alcohol and alkynyl amine at moderate conditions, surpassing the performance of surfactant-protected Ag NPs. X-ray photoelectron spectroscopy and Raman spectral analyses elucidated that strong interactions resulting from the coordination between the nitrogen atoms in the Aza-COF and Ag atoms in Ag NPs prevents their further aggregation and thereby preserving the high activity and recyclability of the composite. This finding demonstrates that the judicious selection of appropriate porous materials to restrict the aggregation of metal particles can yield efficient nanocatalyst composites.

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Section: Resultsmentioning

confidence: 99%

Section: Co 2 Catalytic Conversionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Effective CO₂ Catalytic Conversion by Nitrogen-Rich Covalent Organic Framework-Immobilized Ag Nanoparticles

Li,

Deng,

Wang

et al. 2023

ACS Appl. Nano Mater.

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“…25 The detailed reaction mechanism was studied using DFT calculations by Wang, Yan and co-workers. 26…”

Section: Benzoxazine-2-one From O-alkynylaniline and Carbon Dioxidementioning

confidence: 99%

Silver-catalyzed carboxylation

2016

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Silver-catalyzed reactions are some of the important methodologies in organic chemistry. Since 2007, a new application of silver catalysts has been emerging. For the sequential carboxylation and cyclization of alkyne derivatives, such as propargyl alcohols and amines, using carbon dioxide, silver catalysts show significant reactivity under mild conditions unlike other transition metals. These developments have received much attention for the effective utilization of carbon dioxide in organic chemistry to synthesize heterocyclic compounds. Related silver-catalyzed C-C bond forming reactions with carbon dioxide have also provided the synthetic methods of the corresponding carboxylic acid derivatives. In this review, the recent studies of the silver-catalyzed carboxylation reactions using carbon dioxide are described.

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Addition Reactions: Polar Additions

Knipe¹

2019

Organic Reaction Mechanisms Series

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The reaction mechanism of incorporation of carbon dioxide into o-alkynylaniline derivatives catalyzed by silver salt

Cited by 12 publications

References 34 publications

Effective CO₂ Catalytic Conversion by Nitrogen-Rich Covalent Organic Framework-Immobilized Ag Nanoparticles

Effective CO₂ Catalytic Conversion by Nitrogen-Rich Covalent Organic Framework-Immobilized Ag Nanoparticles

Silver-catalyzed carboxylation

Addition Reactions: Polar Additions

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The reaction mechanism of incorporation of carbon dioxide into o-alkynylaniline derivatives catalyzed by silver salt

Cited by 12 publications

References 34 publications

Effective CO2 Catalytic Conversion by Nitrogen-Rich Covalent Organic Framework-Immobilized Ag Nanoparticles

Effective CO2 Catalytic Conversion by Nitrogen-Rich Covalent Organic Framework-Immobilized Ag Nanoparticles

Silver-catalyzed carboxylation

Addition Reactions: Polar Additions

Contact Info

Product

Resources

About

Effective CO₂ Catalytic Conversion by Nitrogen-Rich Covalent Organic Framework-Immobilized Ag Nanoparticles

Effective CO₂ Catalytic Conversion by Nitrogen-Rich Covalent Organic Framework-Immobilized Ag Nanoparticles