Sulfonic Acid and Ionic Liquid Functionalized Covalent Organic Framework for Efficient Catalysis of the Biginelli Reaction

Yao, Bing‐Jian; Wu, Wen-Xiu; Ding, Luo-Gang; Dong, Yu‐Bin

doi:10.1021/acs.joc.0c02423

Cited by 112 publications

(48 citation statements)

References 62 publications

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“…14,136 Similarly to the synthesis of THQs, these reactions can be catalyzed by Lewis and Brønsted acids such as BF 3 •OEt 2 , 36,40,137-142 BF 3 •O(CH 3 ) 2 , 143,144 FeCl 3 , 145,146 InCl 3 , 147 trifluoromethanesulfonic acid, 148 p-toluenesulfonic acid, 146 CX4SO 3 H, 14,149 TFA, 150,151 camphorsulfonic acid, 152 tris(4-bromophenyl)aminium (TBPA + ), 140,[153][154][155] CBr 4 , 156 iron, 157 copper iodide 158 and iodine. [159][160][161][162][163][164][165][166][167] Furthermore, different triflates have been widely used such as Sc(OTf) 3 , 154,168,169 Yb(OTf) 3 , [170][171][172][173] Cu(OTf) 2 , 174,175 Ce(OTf) 3 , 176,177 Zn(OTf) 2 , 178 AgOTf, 22 In(OTf) 3 179 and Ca(OTf) 2 . 84 Heterogeneous catalysis was also described by using montmorillonite-supported perchloric acid (HClO 4 -Mont).…”

Section: Quinolinesmentioning

confidence: 99%

“…Regarding the reaction medium, various polar and nonpolar solvents have been explored, for example, acetonitrile, 2,4,6,[22][23][24][36][37][38] THF, 159,161 DMSO, 160,162,163,166,173 ethanol, 146,[181][182][183] DMF, 158 acetic acid, 157 dichloromethane, 97,138,145,148,150,179,180,184 TFE, 137,152 diethyl ether, 185 dichloroethane, 140,142,151,153,165,186 chloroform 174 and toluene. 147,171,177 Greener alternatives were also reported such as the absence of a solvent 84,149,174,176,178 or the use of a DES (Scheme 13).…”

Section: Scheme 12 Synthesis Of 2-arylquinoline Derivatives Through A...mentioning

confidence: 99%

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The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

et al. 2022

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Multicomponent Povarov reaction is a powerful approach for the construction of N-heterocyclic containing substances. By using Povarov reaction, in addition to accessing tetrahydroquinolines, quinolines and julolidines in a single step, it is possible to form, respectively, two new Csp3-Csp3 and one Csp3-Nsp3 bonds, two new Csp2-Csp2 and one Csp2-Nsp2 bonds and four Csp3-Csp3 and two Csp3-Nsp1 bonds. This review article reports the main features of the Povarov reaction such as its mechanism, the scope of such reaction concerning to different catalysts and substrates used on it as well as the stereoselective versions of Povarov reaction

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Section: Quinolinesmentioning

confidence: 99%

Section: Scheme 12 Synthesis Of 2-arylquinoline Derivatives Through A...mentioning

confidence: 99%

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

et al. 2022

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“…Very recently, Dong et al examined the catalytic performance of imidazolium and sulfonic acid-modified COF-IM-SO 3 H (monomers: 1,3,5-tri(4-aminophenyl)-benzene (TAPB), 2,5-dimethoxybenzene-1,4-dicarboxaldehyde (DMTPA), and 1-vinylimidazole (VIM)) in terms of the Biginelli reaction with benzaldehyde, ethyl acetoacetate, and urea as reactants. [43] The optimized conditions were screened as the temperature of 90 °C, reaction time of 2.5 h, and 1.0% amount of COF-IM-SO 3 H and the isolated yield of Biginelli adducts reached to 98%. Nevertheless, when the temperature decreased to 25 °C, the yield was only 4%, indicating the catalytic activity was in positive correlation to the reaction temperature.…”

Section: (13 Of 19)mentioning

confidence: 99%

A Rising Star from Two Worlds: Collaboration of COFs and ILs

Zhang

Zhou

et al. 2021

Adv Funct Materials

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The functional composites based on covalent organic frameworks (COFs) and ionic liquids (ILs) have stimulated increasing scientific interest owing to their complementary characteristics and cooperative activation. The tailorability and diversity of COFs and ILs render the COFs‐ILs composites with predesignable structures, extendable syntheses, and customizable functionalities. Although the COFs‐ILs composites have a promising development prospect, thus far, reviews regarding COFs‐ILs composites have not been reported. This minireview summarizes the synthetic strategies including ionothermal synthesis and solvothermal synthesis; in addition, the application performances of meritorious COFs‐ILs composites ranging from catalysis, electrochemistry, adsorption and separation, luminescence sensing, and bio‐related analysis are briefly introduced. Furthermore, this minireview briefly emphasizes the opportunities and challenges faced toward rapidly developed but embryonic COFs‐ILs composites. Altogether, it is expected that this minireview will spark the potential development of COFs‐ILs composites from fundamental synthesis to cutting‐edge applications.

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“…9 They have attracted good interest due to their series of unique properties, such as high specific surface area, low density, high thermal/ chemical stability, and orderly and adjustable pore structure. 10 With the help of flexible monomer replacement, functionalization and composite methods, COFs can successfully tackle challenges in gas storage, 11 catalysis, 12 drug delivery, 13 electrochemistry, 14 separation 15 and fluorescence 16 /chemical sensing. 17 So far, a lot of development and improvement work has been attempted in the application of COFs for the removal of toxic pollutants, especially heavy metal ions.…”

Section: Introductionmentioning

confidence: 99%

Amidinothiourea‐linked covalent organic framework for the adsorption of heavy metal ions

Wang

Feng

Zhang

et al. 2021

Polymer International

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For the first time, a novel amidinothiourea-linked covalent organic framework (COF) (TpAt) has been successfully synthesized by the condensation between 1,3,5-triformylphloroglucinol and amidinothiourea via vacuum solvothermal reaction, and was further utilized for the adsorption of metal ions from aqueous solution. The effects of initial concentration, pH and contact time on the adsorption process were investigated. As a result, the TpAt COF showed maximum binding capacities as high as 95.44, 100.76 and 99.08 mg g -1 for Cr(III), Cd(II) and Cu(II) within 180 min at the initial concentration of 100 mg L -1 , respectively. The isotherms of metal ions onto TpAt could be described by the Freundlich isotherm equation, and the adsorption kinetics followed the pseudo-second-order model. The TpAt could be reused for more than five adsorption-elution cycles, whilst basically maintaining its original adsorption performance and the structural integrity of the COF layers. The robust adsorption efficiency can be attributed to the coordination between metal ions and N, O and S atoms in the TpAt framework. The TpAt COF represents an ideal candidate for the removal of heavy metal ions in environmental pollution treatment.

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Sulfonic Acid and Ionic Liquid Functionalized Covalent Organic Framework for Efficient Catalysis of the Biginelli Reaction

Cited by 112 publications

References 62 publications

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

A Rising Star from Two Worlds: Collaboration of COFs and ILs

Amidinothiourea‐linked covalent organic framework for the adsorption of heavy metal ions

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