1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers as an efficient and reusable nanocatalyst for the synthesis of tetraketones in aqueous medium

Lasemi, Zahra; Tajbakhsh, Mahmood; Alinezhad, Heshmatoallah; Mehrparvar, Forough

doi:10.1007/s11164-020-04167-y

Cited by 17 publications

(7 citation statements)

References 82 publications

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“…The characteristic peak at 1723 cm –1 was assigned to the stretching vibration of the ester carbonyl, which indicated the incorporation of DMAEMA. Moreover, the strong absorption band at 1640 cm –1 was in accordance with the stretching vibration of the CN bond, , which suggested the occurrence of DBU. The signal at 1159 cm –1 could come from the C–N stretching vibration of an aminoalkyl group .…”

Section: Resultsmentioning

confidence: 99%

[HDBU]Br@P-DD as Porous Organic Polymer-Supported Ionic Liquid Catalysts for Chemical Fixation of CO₂ into Cyclic Carbonates

Zheng

Qiu

et al. 2023

ACS Sustainable Chem. Eng.

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The chemical fixation of CO2 into high value-added cyclic carbonates is of significant potential and sustainability to address the energy and ecological issues. [HDBU]Br@P-DD-m/n, a series of porous organic polymer-supported ionic liquids (PSILs), were fabricated in this work through a one-pot four-component reaction of DMAEMA, DVB, 4-bromobutyric acid, and DBU. The formation of [HDBU]Br and construction of the P-DD polymer network proceeded concurrently with the support of the in situ-formed IL being achieved simultaneously. Characterization of the PSILs by IR, ICP, BET, SEM, and TGA etc. showed that the as-prepared catalysts possessed versatile hierarchical porosity with varying ionic densities and excellent thermostability. The porosity of the copolymer skeleton was found to be affected by the accompanying formation of [HDBU]Br. The PSILs were then evaluated as catalysts for the cycloaddition reaction of CO2 with epoxides, among which [HDBU]Br@P-DD-4/1 showed the optimal performance under atmospheric pressure and solvent-/cocatalyst-free conditions (95% yield and 99% selectivity for CO2 cycloaddition with epichlorohydrin). By correlating the performance and structures of the catalysts, the synergistic effect of the tertiary amine, [HDBU]Br, and pore distribution was demonstrated. In addition, the catalyst was found to be applicable in synthesizing a range of differently substituted carbonates in good to excellent yields. Finally, the catalyst could be recovered readily and good catalytic activity was still observed after use for 6 runs. The work not only provided an active, reusable, and metal-free heterogeneous catalyst for the fixation of CO2 into cyclic carbonates but also developed a facile one-step multicomponent strategy for constructing PSIL catalysts, which would be promising to find wide applications in catalysis and organic synthesis field.

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Section: Resultsmentioning

confidence: 99%

[HDBU]Br@P-DD as Porous Organic Polymer-Supported Ionic Liquid Catalysts for Chemical Fixation of CO₂ into Cyclic Carbonates

Zheng

Qiu

et al. 2023

ACS Sustainable Chem. Eng.

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“… Entry Ar Product Time (min) Yield (%) a M. P. (Lit. mp) (°C) 39 , 56 1 C 6 H 5 6a 15 98 228–230 (227) 2 3-NO 2 C 6 H 4 6b 12 94 207–209 (209) 3 4-CH 3 C 6 H 4 6c 15 94 212–213 (212) 4 4-CH 3 OC 6 H 4 6d 18 95 201–202 (202) 5 4-ClC 6 H 4 6e 8 97 206–208 (207) 6 4-BrC 6 H 4 6f. 10 95 199–200 (197) 7 C 6 H 5 8a 20 95 260–262 (261) 8 3-NO 2 C 6 H 4 8b 25 94 258–259 (258) 9 4-NO 2 ...…”

Section: Resultsmentioning

confidence: 99%

Heteropolyacid coupled with cyanoguanidine decorated magnetic chitosan as an efficient catalyst for the synthesis of pyranochromene derivatives

Rahimzadeh

Tajbakhsh

Daraie

et al. 2022

Sci Rep

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In this study, a novel nanocatalyst was successfully prepared by heteropolyacid immobilization of magnetic chitosan-cyanoguanidine composite and fully characterized by different analysis methods, including FTIR, XRD, TGA, SEM, and EDS. The catalytic activity of fabricated composite was examined in a one-pot three-component reaction, involving the diverse active methylene compounds, various aryl aldehydes, and malononitrile in water. The results revealed the efficient catalytic performance of composite, while all reactions proceeded smoothly and led to the formation of the corresponding pyranochromene derivatives in high to excellent yields.

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“…Lasemi et al [43] prepared heterogeneous 8-Diazabicyclo[5,4,0]undec-7-ene functionalized cellulose nanofibers (CNF@DBU[Cl]) and employed it as a catalyst (0.08 g) in the synthesis of bisdimedone derivatives by the reaction of dimedone with various kinds of aldehydes via Knoevenagel-Michael reaction in the presence of water as a solvent at the room temperature. This pathway involved several advantages such as reusability of catalyst up to 4 cycles, high yields of products (80%-96%), mild reaction conditions, short reaction time, wide scope of aldehydes, simple work-up and avoidance of harmful solvents (Scheme 4: Method 3).…”

Section: Synthesis Of Bisdimedones Using Nanomaterials Based Catalystmentioning

confidence: 99%

Advancement in synthetic strategies of bisdimedones: Two decades study

Teli¹,

Sahiba²,

Sethiya³

et al. 2021

Journal of Heterocyclic Chem

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Bisdimedones have emerged as an important and versatile moiety in the field of synthetic and medicinal chemistry. It is screened as a precursor for the synthesis of several heterocycles such as acridinediones, xanthenediones, thioxanthenes, and benzopyrans that exhibited immense pharmacological as well as industrial applications. Its extensive characteristics have attracted the scientists to develop various protocols for the synthesis of bisdimedones and their derivatives from the reaction of dimedone with several aldehydes under different environmental conditions using various types of catalysts. This review encapsulates the recent progress in the synthesis of bisdimedone derivatives under several reaction protocols such as the use of nanoparticles, ionic liquids, metal salts, simple organic compounds, and catalyst-free conditions, and so forth in the last 20 years.

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1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers as an efficient and reusable nanocatalyst for the synthesis of tetraketones in aqueous medium

Cited by 17 publications

References 82 publications

[HDBU]Br@P-DD as Porous Organic Polymer-Supported Ionic Liquid Catalysts for Chemical Fixation of CO₂ into Cyclic Carbonates

[HDBU]Br@P-DD as Porous Organic Polymer-Supported Ionic Liquid Catalysts for Chemical Fixation of CO₂ into Cyclic Carbonates

Heteropolyacid coupled with cyanoguanidine decorated magnetic chitosan as an efficient catalyst for the synthesis of pyranochromene derivatives

Advancement in synthetic strategies of bisdimedones: Two decades study

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1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers as an efficient and reusable nanocatalyst for the synthesis of tetraketones in aqueous medium

Cited by 17 publications

References 82 publications

[HDBU]Br@P-DD as Porous Organic Polymer-Supported Ionic Liquid Catalysts for Chemical Fixation of CO2 into Cyclic Carbonates

[HDBU]Br@P-DD as Porous Organic Polymer-Supported Ionic Liquid Catalysts for Chemical Fixation of CO2 into Cyclic Carbonates

Heteropolyacid coupled with cyanoguanidine decorated magnetic chitosan as an efficient catalyst for the synthesis of pyranochromene derivatives

Advancement in synthetic strategies of bisdimedones: Two decades study

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Product

Resources

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[HDBU]Br@P-DD as Porous Organic Polymer-Supported Ionic Liquid Catalysts for Chemical Fixation of CO₂ into Cyclic Carbonates

[HDBU]Br@P-DD as Porous Organic Polymer-Supported Ionic Liquid Catalysts for Chemical Fixation of CO₂ into Cyclic Carbonates