Metal-free heterogeneous and mesoporous biogenic graphene-oxide nanoparticle-catalyzed synthesis of bioactive benzylpyrazolyl coumarin derivatives

Siddiqui, Tabassum; Ghule, Balaji G.; Shaikh, Shoyebmohamad F.; Shinde, Pritamkumar V.; Gunturu, Krishna Chaitanya; Zubaidha, P. K.; Yun, Jinwon; O’Dwyer, Colm; Mane, Rajaram S.; Kim, Kwang Ho

doi:10.1039/c7ra12550j

Cited by 27 publications

(13 citation statements)

References 41 publications

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“…Graphene oxide (GO), a 2D, carbonaceous material bearing different oxygen functional groups such as alcohol, epoxide, ketones, and carboxylic acid 9–12 , is emerging as a green alternative for organic transformations and particularly superb in acidic carbocatalysis 5,13,14 . The inherent Brønsted acidity of GO, due to the presence of acidic oxygen groups on the edge of GO sheets, has been well exploited in the synthesis of benzylpyrazolyl coumarins 15 , thioacetals 16 , ethers 17 , and other Brønsted acid-catalyzed reactions such as transamidation 18 , Fisher esterification 19–22 , Boc-protection of alcohols 23 , and Kabachnik-Fields reactions 24 . Despite these extensive studies, only the Brønsted acidic nature of GO was recognized.…”

Section: Introductionmentioning

confidence: 99%

Regenerable Acidity of Graphene Oxide in Promoting Multicomponent Organic Synthesis

Ebajo

Santos

Alea

et al. 2019

Sci Rep

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The Brønsted acidity of graphene oxide (GO) materials has shown promising activity in organic synthesis. However, roles and functionality of Lewis acid sites remain elusive. Herein, we reported a carbocatalytic approach utilizing both Brønsted and Lewis acid sites in GOs as heterogeneous promoters in a series of multicomponent synthesis of triazoloquinazolinone compounds. The GOs possessing the highest degree of oxidation, also having the highest amounts of Lewis acid sites, enable optimal yields (up to 95%) under mild and non-toxic reaction conditions (85 °C in EtOH). The results of FT-IR spectroscopy, temperature-programed decomposition mass spectrometry, and X-ray photoelectron spectroscopy identified that the apparent Lewis acidity via basal plane epoxide ring opening, on top of the saturated Brønsted acidic carboxylic groups, is responsible for the enhanced carbocatalytic activities involving Knoevenagel condensation pathway. Recycled GO can be effectively regenerated to reach 97% activity of fresh GO, supporting the recognition of GO as pseudocatalyst in organic synthesis.

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Section: Introductionmentioning

confidence: 99%

Regenerable Acidity of Graphene Oxide in Promoting Multicomponent Organic Synthesis

Ebajo

Santos

Alea

et al. 2019

Sci Rep

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“…The presence of carboxyl groups boosts ipso-hydroxylation as revealed by the control experiments, and GO can be reused several times without losing its activity. Furthermore, GO has been successfully utilized as a green carbocatalyst for the synthesis of numerous biologically relevant scaffolds such as benzylbarbiturocoumarin derivatives [169], 3-dihydroquinazolinones and quinazolin-4-(3H)-ones [170] and benzylpyrazolyl coumarin derivatives [171], 2,5-dimethyl-N-phenyl pyrrole [172], poly heterocyclic spiro-indeno quinoxaline pyrrolizidines quinoxalin and spiro-oxindoles pyrrolizidines [173], 3-sulfenylimidazo[1,2-a]pyridines [174], dihydro-2-oxopyrroles [175], etc. Roy et al [176] developed an eco-friendly method for the synthesis of library of bioactive nitrogen containing heterocycles, quinoxalines [177] from 2-nitroanilines under entirely metal-free conditions using GO or rGO as a green catalyst (Scheme 12).…”

Section: Ionic Liquid Supported On Go As Catalystmentioning

confidence: 99%

Recent advances in the catalytic applications of GO/rGO for green organic synthesis

Sachdeva

2020

Green Processing and Synthesis

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Graphene is considered a promising catalyst candidate due to its 2D nature, single-atom thickness, zero bandgap and very high surface to volume ratio. Further, graphene oxide (GO) has been used as a catalytic support material for metal/metal oxide nanoparticles due to its tunable electrical properties. In addition, its high chemical stability and ultrahigh thermal conductivity may possibly promote high loading of catalytically active sites. This review article focuses on the recent progress in the catalytic applications of GO especially (i) as catalytic-support material (GO/reduced graphene oxide supported metal/metal oxide nanohybrids) for the green synthesis of biologically relevant molecules, (ii) for metal-free catalysis and (iii) for electrocatalysis, with special focus on graphene contribution to catalytic efficiency. The critical overview and future perspectives are also discussed.

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“…Huang group exploited the synergistic effect of Ruthenium and Rhodium supported by TiO 2 nanotube (TNT's) systems in the hydroformylations of vinyl acetate and cyclohexene (Scheme ) . The loading of Rh was 2% while Ru was maintained at 0.5% from ICP analysis.…”

Section: Catalysis Using Heterobimetallic Nanoparticle Catalystsmentioning

confidence: 99%

Synthetic Organic Transformations of Transition‐Metal Nanoparticles as Propitious Catalysts: A Review

Ganesh

Ramakrishna

2020

Asian J Org Chem

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Nanotechnology has produced compelling evidences in the field of catalysis, construction, electronics, energy, food, imaging, medical, packaging, pharmaceutical sectors and in water treatment. Nanoparticles of transition metal origin are enticing in catalytic applications due to their lowlying empty orbitals for bonding and can offer a distinct ability to expand the coordination sphere. This coupled with ease of synthesis, recyclability and occurrence in abundance staples them as unique industrial materials. Transition metals such as Gold, Palladium, Silver, Copper, Iron, Ruthenium, Rhodium and hetero-bimetallic versions have been in demand for various organic transformations. The sharp rise in number of literature reports justifies the stand in catalytic property. A unique ability to form Covalent and/or Van der Waals interactions with solid supports and activate the substrates through close functional group interactions renders them as effective entities in organic transformations. In this review, we present the new developments in this niche in the past five years with a retreat on the mechanistic aspects along with parameters involved in nanoparticle characterizations through advances in spectroscopy.

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Metal-free heterogeneous and mesoporous biogenic graphene-oxide nanoparticle-catalyzed synthesis of bioactive benzylpyrazolyl coumarin derivatives

Abstract: Graphene oxide catalyst, obtained by table sugar carbonization, is envisaged for the synthesis of bio-active benzylpyrazolyl coumarin derivatives with considerable yield and remarkable re-usability.

Cited by 27 publications

References 41 publications

Regenerable Acidity of Graphene Oxide in Promoting Multicomponent Organic Synthesis

Regenerable Acidity of Graphene Oxide in Promoting Multicomponent Organic Synthesis

Recent advances in the catalytic applications of GO/rGO for green organic synthesis

Synthetic Organic Transformations of Transition‐Metal Nanoparticles as Propitious Catalysts: A Review

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