Highly Efficient Synthesis of Quinazoline-2,4(1H,3H)-diones from CO2 by Hydroxyl Functionalized Aprotic Ionic Liquids

Shi, Guiling; Chen, Kaihong; Wang, Yongtao; Li, Haoran; Wang, Congmin

doi:10.1021/acssuschemeng.8b01109

Cited by 62 publications

(45 citation statements)

References 57 publications

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“…A hydroxyl functionalized aprotic ionic liquid shows high efficiency in synthesis of quinazoline-2,4(1H,3H) -diones from atmospheric CO 2 . The captured CO 2 instead of atmospheric CO 2 is also used and only 13% yield is obtained, being ascribed to the strong interaction between [Im] − and CO 2 (Scheme 11) (Shi et al, 2018). They also demonstrates the feasibility of using captured CO 2 as starting material in their another report, where the CO 2 captured by azole-type anion [DEIm] − renders a high yield of alkylidene carbonates in the carboxylative cyclization of propargyl alcohol due to the weak interaction between CO 2 and the anion (Scheme 11) (Chen et al, 2016).…”

Section: Ionic Liquids (Ils)mentioning

confidence: 99%

CO2 Capture and in situ Catalytic Transformation

You

et al. 2019

Front. Chem.

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The escalating rate of fossil fuel combustion contributes to excessive CO 2 emission and the resulting global climate change has drawn considerable attention. Therefore, tremendous efforts have been devoted to mitigate the CO 2 accumulation in the atmosphere. Carbon capture and storage (CCS) strategy has been regarded as one of the promising options for controlling CO 2 build-up. However, desorption and compression of CO 2 need extra energy input. To circumvent this energy issue, carbon capture and utilization (CCU) strategy has been proposed whereby CO 2 can be captured and in situ activated simultaneously to participate in the subsequent conversion under mild conditions, offering valuable compounds. As an alternative to CCS, the CCU has attracted much concern. Although various absorbents have been developed for the CCU strategy, the direct, in situ chemical conversion of the captured CO 2 into valuable chemicals remains in its infancies compared with the gaseous CO 2 conversion. This review summarizes the recent progress on CO 2 capture and in situ catalytic transformation. The contents are introduced according to the absorbent types, in which different reaction type is involved and the transformation mechanism of the captured CO 2 and the role of the absorbent in the conversion are especially elucidated. We hope this review can shed light on the transformation of the captured CO 2 and arouse broad concern on the CCU strategy.

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Section: Ionic Liquids (Ils)mentioning

confidence: 99%

CO2 Capture and in situ Catalytic Transformation

You

et al. 2019

Front. Chem.

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“…However, almost all the reported IL systems involve high usage amounts of dual catalyst-solvent media (>1.0 equiv.). There were no intensive and systematic research figuring out the role of the IL, such as the effects of cation and anion until Dyson’s work [80] and Wang’s work [81] was published (Scheme 12).…”

Section: Chemical Fixation Of Co2 Through C-n Bond Formationmentioning

confidence: 99%

“…On the other hand, according to quantum-chemical calculations, NMR spectroscopic investigations and controlled experiments, Wang et al proposed that the basicity of cation affects the catalytic activity of ILs dramatically (Figure 4) [81]. In addition, the cation with more OH groups exhibited poorer catalytic activity.…”

Section: Chemical Fixation Of Co2 Through C-n Bond Formationmentioning

confidence: 99%

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Catalytic Conversion of Carbon Dioxide through C-N Bond Formation

Song

Zhang

et al. 2019

Molecules

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From the viewpoint of green chemistry and sustainable development, it is of great significance to synthesize chemicals from CO2 as C1 source through C-N bond formation. During the past several decade years, many studies on C-N bond formation reaction were involved, and many efforts have been made on the theory. Nevertheless, several great challenges such as thermodynamic limitation, low catalytic efficiency and selectivity, and high pressure etc. are still suffered. Herein, recent advances are highlighted on the development of catalytic methods for chemical fixation of CO2 to various chemicals through C-N bond formation. Meanwhile, the catalytic systems (metal and metal-free catalysis), strategies and catalytic mechanism are summarized and discussed in detail. Besides, this review also covers some novel synthetic strategies to urethanes based on amines and CO2. Finally, the regulatory strategies on functionalization of CO2 for N-methylation/N-formylation of amines with phenylsilane and heterogeneous catalysis N-methylation of amines with CO2 and H2 are emphasized.

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“…Recently, Wang et al developed an efficient strategy for generation of quinazoline-2,4(1H,3H)-diones from CO 2 through varying the cations to design hydroxyl functionalized ILs, in which the catalytic activity is affected by the basicity of cation and the hydrogen bond from cation shows great promotion for this reaction (Shi et al, 2018 ). The aprotic IL (2-hydroxyethyl)-trimethyl-ammonium imidazole, [Ch][Im], gives the best catalytic activity.…”

Section: Ionic Liquid Catalysis For Co 2 Conversiomentioning

confidence: 99%

Ionic Liquids Catalysis for Carbon Dioxide Conversion With Nucleophiles

Xia

Chen

et al. 2018

Front. Chem.

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Carbon dioxide, as a promising C1 synthon, has attracted great interest in organic synthesis. Due to the thermodynamic stability and kinetic inertness of CO2, developing efficient strategies for CO2 activation and subsequent conversion is very crucial. In this context, Ionic liquids (ILs) show great potential for capturing and activating CO2 owing to their unique structures and properties, making them become ideal alternatives to volatile organic solvents and/or catalysts for CO2 transformation. This minireview aims at summarizing ILs-promoted reactions of CO2 with N-nucleophiles (primary amines)/O-nucleophiles (primary alcohols, water). Two catalytic systems i.e., metal/ILs binary systems such as Cu/ILs systems and Ag/ILs systems as well as single ILs systems including anion-functionalized ILs and bifunctionalized ILs have been developed for CO2 catalytic conversion, for instance, carboxylative cyclization of nucleophiles e.g., propargylic alcohols, amines, 2-aminobenzonitriles and o-aminobenzenethiol, and formylation of amines or 2-aminothiophenols with hydrosilanes to afford various value-added chemicals e.g., cyclic carbamates, unsymmetrical organic carbonates, α-hydroxyl ketones, and benzimidazolones. In a word, IL could provide a powerful tool for efficient CO2 utilization.

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Highly Efficient Synthesis of Quinazoline-2,4(1H,3H)-diones from CO₂ by Hydroxyl Functionalized Aprotic Ionic Liquids

Cited by 62 publications

References 57 publications

CO2 Capture and in situ Catalytic Transformation

CO2 Capture and in situ Catalytic Transformation

Catalytic Conversion of Carbon Dioxide through C-N Bond Formation

Ionic Liquids Catalysis for Carbon Dioxide Conversion With Nucleophiles

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