Amino-grafted Cu and Sc Metal-Organic Frameworks involved in the green synthesis of 2-amino-4H-chromenes. Mechanistic understanding

González-Rodal, D.; Palomino, Gemma Turnes; Cabello, Carlos Palomino; Pérez‐Mayoral, Elena

doi:10.1016/j.micromeso.2021.111232

Cited by 7 publications

(3 citation statements)

References 53 publications

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“…Nevertheless, metals as part of MOFs are uniformly and precisely distributed along their structures, often being the main active sites. In addition, other functional groups introduced into the MOF structure from either a carefully selected organic linker or by grafting (e.g., amines) by using the post-synthetic method [6] can be present.…”

Section: Introductionmentioning

confidence: 99%

Opportunities from Metal Organic Frameworks to Develop Porous Carbons Catalysts Involved in Fine Chemical Synthesis

et al. 2023

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In the last decade, MOFs have been proposed as precursors of functional porous carbons with enhanced catalytic performances by comparison with other traditional carbonaceous catalysts. This area is rapidly growing mainly because of the great structural diversity of MOFs offering almost infinite possibilities. MOFs can be considered as ideal platforms to prepare porous carbons with highly dispersed metallic species or even single-metal atoms under strictly controlled thermal conditions. This review briefly summarizes synthetic strategies to prepare MOFs and MOF-derived porous carbons. The main focus relies on the application of the MOF-derived porous carbons to fine chemical synthesis. Among the most explored reactions, the oxidation and reduction reactions are highlighted, although some examples of coupling and multicomponent reactions are also presented. However, the application of this type of catalyst in the green synthesis of biologically active heterocyclic compounds through cascade reactions is still a challenge.

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Section: Introductionmentioning

confidence: 99%

Opportunities from Metal Organic Frameworks to Develop Porous Carbons Catalysts Involved in Fine Chemical Synthesis

et al. 2023

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“…Multicomponent reactions (MCR) provision deep knowledge regarding 4H-chromene formation. Furthermore, considerable catalytic schemes have evolved over recent years for the multicomponent synthesis of 4H-chromene derivatives, including RGO-SO 3 H 59 , GO/α-Fe 2 O 3 /CuL 60 , MNPs@Cu 61 , g-C 3 N 4 62 , Pd@g-C 3 N 4 63 , CaMgFe 2 O 4 64 , morpholine 65 , CAEDA 66 , mica/Fe 3 O 4 67 , amino grafted MOFs 68 , DABCO 69 , Fe 3 O 4 @Sal@Cu 70 , Fe 3 O 4 @GO-NH 71 , KCC-1@NH 2 72 , Nano-SiO 2 73 , SnO 2 NPs 74 , Ag 2 O/GO/TiO 2 75 , and borax 76 . Yet, there are several drawbacks concerning plenty of expressed catalysts, including environmental contamination, high price, challenging catalyst removal, and requiring coarse reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

CSA@g-C3N4 as a novel, robust and efficient catalyst with excellent performance for the synthesis of 4H-chromenes derivatives

Hosseini,

Azizi

2023

Sci Rep

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A pioneering robust and green heterogeneous acidic catalyst (CSA@g-C3N4) was rationally designed via immobilization of camphorsulfonic acid (CSA) on the g-C3N4 surface under mild conditions. Grafting CSA in the g-C3N4 lattice is distinguished as the root cause of facilitating the structure change of g-C3N4, leading to a unique morphology, accordingly the remarkable catalytic efficiency of CSA@g-C3N4. The morphology of new as-prepared nano-catalyst was specified by means of FT-IR, XRD, SEM, EDS, TEM, TGA, and BET. For the first time, it is exhibited that the efficient catalyst CSA@g-C3N4 can productively accomplish the three-component reactions with high yields and also serve as an inspiration for easily performing various sorts of MCRs based on our finding. The recommended synthesis pathway of chromenes derivatives is facile and cost-effective which applies a condensation reaction of salicylaldehyde, thiophenol, and malononitrile followed by ready purification in a benign manner. Moreover, the CSA@g-C3N4 nanocomposite can be promptly reused, illustrating no sensational decrease in the catalytic activity after ten times.

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“…However, the synthesis of 4 H ‐chromenes in the presence of catalytically active ionic liquids and M x Sr 2 Nb 2 O 7+δ (M=Cr 3+ , Cu 2+ , Zn 2+ , Ag + , and Cd 2+ ) nanocomposites under microwave and ultrasound irradiations, [12a–c] respectively, has reduced some of the drawbacks. Three recent studies have focused on describing methods for the synthesis of 4 H ‐chromenes in high yields and short reaction times using small amounts of easily prepared heterogeneous catalysts, including amino‐grafted Cu and Sc Metal‐Organic Frameworks (MOFs), [12d] immobilized piperazine on the surface of graphene oxide (GO), [12e] and cyclometrix polyphosphazenes (cPOPs) [12f] . Thus, the development of sustainable, low‐cost, and efficient heterogeneous catalysts to synthesize 4 H ‐chromenes using non‐traditional heating methods is still of great interest in organic synthesis and drug discovery.…”

Section: Introductionmentioning

confidence: 99%

Solvent‐Free Microwave‐Assisted Multicomponent Synthesis of 4H‐Chromenes Using Fe₃O₄‐Based Hydrotalcites as Bifunctional Catalysts

et al. 2022

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Magnetic Fe 3 O 4 -based hydrotalcites were used as bifunctional catalysts for the microwave-assisted solvent-free synthesis of 4H-chromene derivatives by a three-component reaction from (hetero)aromatic aldehydes, malononitrile, and naphthol derivatives. Structures of 4H-chromenes 4 d and 4 g were studied and confirmed by single-crystal X-ray diffraction analysis. The heterogeneous catalysts were synthesized by the co-precipitation method incorporating divalent metal cations such as Ni 2 + or Co 2 + in LDHÀ Mg. This multicomponent protocol allows the synthesis of diverse 4H-chromenes in 88-95 % yields, reduced reaction time, high atom economy, broad substrate scope, and operational simplicity. The reusability of the catalyst up to five recycles without appreciable loss of its catalytic activity, make the present protocol sustainable and advantageous compared to conventional methods.

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Amino-grafted Cu and Sc Metal-Organic Frameworks involved in the green synthesis of 2-amino-4H-chromenes. Mechanistic understanding

Cited by 7 publications

References 53 publications

Opportunities from Metal Organic Frameworks to Develop Porous Carbons Catalysts Involved in Fine Chemical Synthesis

Opportunities from Metal Organic Frameworks to Develop Porous Carbons Catalysts Involved in Fine Chemical Synthesis

CSA@g-C3N4 as a novel, robust and efficient catalyst with excellent performance for the synthesis of 4H-chromenes derivatives

Solvent‐Free Microwave‐Assisted Multicomponent Synthesis of 4H‐Chromenes Using Fe₃O₄‐Based Hydrotalcites as Bifunctional Catalysts

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Amino-grafted Cu and Sc Metal-Organic Frameworks involved in the green synthesis of 2-amino-4H-chromenes. Mechanistic understanding

Cited by 7 publications

References 53 publications

Opportunities from Metal Organic Frameworks to Develop Porous Carbons Catalysts Involved in Fine Chemical Synthesis

Opportunities from Metal Organic Frameworks to Develop Porous Carbons Catalysts Involved in Fine Chemical Synthesis

CSA@g-C3N4 as a novel, robust and efficient catalyst with excellent performance for the synthesis of 4H-chromenes derivatives

Solvent‐Free Microwave‐Assisted Multicomponent Synthesis of 4H‐Chromenes Using Fe3O4‐Based Hydrotalcites as Bifunctional Catalysts

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Solvent‐Free Microwave‐Assisted Multicomponent Synthesis of 4H‐Chromenes Using Fe₃O₄‐Based Hydrotalcites as Bifunctional Catalysts