Chemoselective reduction of quinoline over Rh–C<sub>60</sub> nanocatalysts

Luo, Zhishan; Min, Yuanyuan; Nechiyil, Divya; Bacsa, Wolfgang; Tison, Yann; Martínez, Hervé; Lecante, Pierre; Gerber, Iann C.; Serp, Philippe; Axet, M. Rosa

doi:10.1039/c9cy02025j

Cited by 21 publications

(18 citation statements)

References 74 publications

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“…For example, Wang et al reported the successful application of a catalyst based on Ru single atoms in the UiO-66 metal–organic framework (MOF) for the catalytic hydrogenation of quinolone . Recently, Luo et al used Rh nanoparticles supported on fullerene C 60 to achieve excellent activity and selectivity toward the synthesis of 1,2,3,4-tetrahydroquinoline (py-THQ) . However, catalysts supported on solids must be separated from the products after the reaction through filtration, centrifugation, or precipitation .…”

Section: Introductionmentioning

confidence: 99%

“…11 Recently, Luo et al used Rh nanoparticles supported on fullerene C 60 to achieve excellent activity and selectivity toward the synthesis of 1,2,3,4tetrahydroquinoline (py-THQ). 17 However, catalysts supported on solids must be separated from the products after the reaction through filtration, centrifugation, or precipitation. 5 These T h i s c o n t e n t i s processes severely affect the reusability of catalysts due to a gradual and significant loss of the catalyst in each cycle.…”

Section: ■ Introductionmentioning

confidence: 99%

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Co₃O₄/Nitrogen-Doped Graphitic Carbon/Fe₃O₄ Nanocomposites as Reusable Catalysts for Hydrogenation of Quinoline, Cinnamaldehyde, and Nitroarenes

Shaikh

Abdelnaby

Hakeem

et al. 2021

ACS Appl. Nano Mater.

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Developing efficient, robust, and highly recyclable catalysts with the ability to separate products conveniently for industrially important hydrogenation reactions is a major challenge. Edges of nanoparticles possessing selective catalytic properties while the completely exposed metal particles are devoid of this attribute is a known fact. Herein, the preparation and evaluation of a Co 3 O 4 /N-Gr/Fe 3 O 4 magnetic heterostructure composed of Co 3 O 4 nanoparticles surrounded by nitrogen-doped graphitic carbon derived from ZIF-67 on an Fe 3 O 4 support is described. Wrapping Co 3 O 4 nanoparticles with porous nitrogen-rich graphitic carbon increases their catalytic selectivity and durability. Co 3 O 4 /N-Gr/Fe 3 O 4 is obtained by pyrolysis of metal−organic frameworks, ZIF-67(Co) with magnetic Fe 3 O 4 nanoparticles under nitrogen. Scanning electron microscopy reveals Fe 3 O 4 as uniform octagonal microcrystals (∼450 nm) and transmission electron microscopy (TEM) shows graphitic carbon layers around the core Co 3 O 4 nanoparticles on Fe 3 O 4 microcrystals. TEM using a high-angle annular dark-field with spherical aberration (Cs) correction shows the core−shell structure of Co 3 O 4 /N-Gr nanocrystals (∼20 nm) with the graphitic carbon layers surrounding the core Co 3 O 4 nanoparticles on Fe 3 O 4 microcrystals. The resulting Co 3 O 4 /N-Gr/Fe 3 O 4 construct produces a stable and reusable catalyst for the selective hydrogenation of structurally diverse N-heteroarenes. Particularly, quinoline was quantitatively hydrogenated to 1,2,3,4-tetrahydroquinoline (py-THQ) at 120 °C under 40 bar of H 2 . The wide applicability of Co 3 O 4 /N-Gr/Fe 3 O 4 was tested for selective hydrogenation of cinnamaldehyde to hydrocinnamaldehyde (HCAL) with >99% selectivity. Also, the tolerance of functional groups in the reduction of nitroarene was evaluated. The benefit of the ability to produce py-THQ was demonstrated by extending the protocol for the synthesis of bioactive molecules, that is, a tubulin polymerization inhibitor with a 94% yield. The robust nature of the Co 3 O 4 /N-Gr/ Fe 3 O 4 construct was demonstrated through multiple cycles of simple separation and reuse.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Co₃O₄/Nitrogen-Doped Graphitic Carbon/Fe₃O₄ Nanocomposites as Reusable Catalysts for Hydrogenation of Quinoline, Cinnamaldehyde, and Nitroarenes

Shaikh

Abdelnaby

Hakeem

et al. 2021

ACS Appl. Nano Mater.

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“…Taking into consideration this previous result, we examine here the possibility of using Ru/PVP catalysts to directly transform furfural into 1,2-PeD. Knowing that this transformation is sensitive to support effects [9,14,15] and our experience of tuning activity and selectivity in catalysed reactions by changing the adsorbates on the metallic surfaces [30][31][32][33], we have studied the effect of the in situ addition of organic ligands in order to examine their impact in the outcome of this chemical transformation. The modulation of the catalytic properties of heterogeneous catalysts using surface adsorbates is an important field in catalysis, yet it is in its infancy [34].…”

Section: Introductionmentioning

confidence: 99%

In Situ Ruthenium Catalyst Modification for the Conversion of Furfural to 1,2-Pentanediol

et al. 2022

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Exploiting biomass to synthesise compounds that may replace fossil-based ones is of high interest in order to reduce dependence on non-renewable resources. 1,2-pentanediol and 1,5-pentanediol can be produced from furfural, furfuryl alcohol or tetrahydrofurfuryl alcohol following a metal catalysed hydrogenation/C-O cleavage procedure. Colloidal ruthenium nanoparticles stabilized with polyvinylpyrrolidone in situ modified with different organic compounds are able to produce 1,2-pentanediol directly from furfural in a 36% of selectivity at 125 °C under 20 bar of H2 pressure.

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“…On the other hand, hydrides of N-heteroarenes, which are obtained by the hydrogenation of aromatics, play an important role in the agrochemical and pharmaceutical industries. − Recently, a heterogeneous catalysis system applied in such processes undergo rapid development. − Notably, catalysts supported by noble metals, such as Ru, Rh, and Ir, provide a good catalytic platform and are successfully used in different aromatic hydrogenation reactions. − However, most of the studies on these processes concentrate on a simple model reaction. , The molecules often have more intricate structures in practical industry applications. Consequently, rational design and synthesis of supported metal catalysts with superb mass enrichment combined with excellent active sites are of equal importance for the catalytic reactions in pharmaceutical industries.…”

Section: Introductionmentioning

confidence: 99%

Cu Nanoclusters Anchored on the Metal–Organic Framework for the Hydrolysis of Ammonia Borane and the Reduction of Quinolines

et al. 2021

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Free-access active sites created and the interaction regulated between them and substrates during the heterogeneous catalysis process are crucial, which remain a great challenge. In this work, in suit reduced to afford naked Cu nanoparticles (NPs) have been anchored on the metal–organic framework (MOF), NH2-MOF, to form Cu-NH2-MOF. The strategy can precisely control the Cu NP formation with small size and uniform distribution. The Cu NP properties and MOF advantages have been integrated to create a great catalyst with multiple functions and have resulted in improving the recyclability and superb catalytic activity for the one-pot reduction of heterocycle reactions under mild conditions. The experimental and theoretical calculation results show that the superior performance should be attributed to the framework of NH2-MOF that provides large caves for substrate enrichment and the stabilization of Cu sites by the −NH2 group.

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Chemoselective reduction of quinoline over Rh–C₆₀ nanocatalysts

Abstract: Highly selective hydrogenation of quinoline by electron-deficient Rh species containing fullerene.

Cited by 21 publications

References 74 publications

Co₃O₄/Nitrogen-Doped Graphitic Carbon/Fe₃O₄ Nanocomposites as Reusable Catalysts for Hydrogenation of Quinoline, Cinnamaldehyde, and Nitroarenes

Co₃O₄/Nitrogen-Doped Graphitic Carbon/Fe₃O₄ Nanocomposites as Reusable Catalysts for Hydrogenation of Quinoline, Cinnamaldehyde, and Nitroarenes

In Situ Ruthenium Catalyst Modification for the Conversion of Furfural to 1,2-Pentanediol

Cu Nanoclusters Anchored on the Metal–Organic Framework for the Hydrolysis of Ammonia Borane and the Reduction of Quinolines

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Chemoselective reduction of quinoline over Rh–C60 nanocatalysts

Abstract: Highly selective hydrogenation of quinoline by electron-deficient Rh species containing fullerene.

Cited by 21 publications

References 74 publications

Co3O4/Nitrogen-Doped Graphitic Carbon/Fe3O4 Nanocomposites as Reusable Catalysts for Hydrogenation of Quinoline, Cinnamaldehyde, and Nitroarenes

Co3O4/Nitrogen-Doped Graphitic Carbon/Fe3O4 Nanocomposites as Reusable Catalysts for Hydrogenation of Quinoline, Cinnamaldehyde, and Nitroarenes

In Situ Ruthenium Catalyst Modification for the Conversion of Furfural to 1,2-Pentanediol

Cu Nanoclusters Anchored on the Metal–Organic Framework for the Hydrolysis of Ammonia Borane and the Reduction of Quinolines

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Product

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Chemoselective reduction of quinoline over Rh–C₆₀ nanocatalysts

Co₃O₄/Nitrogen-Doped Graphitic Carbon/Fe₃O₄ Nanocomposites as Reusable Catalysts for Hydrogenation of Quinoline, Cinnamaldehyde, and Nitroarenes

Co₃O₄/Nitrogen-Doped Graphitic Carbon/Fe₃O₄ Nanocomposites as Reusable Catalysts for Hydrogenation of Quinoline, Cinnamaldehyde, and Nitroarenes