Palladium oxide nanoparticles intercalated mesoporous silica for solvent free acceptorless dehydrogenation reactions of alcohols

Samanta, Partha; Ray, Shounak; Das, Trisha; Gage, Samuel H.; Nandi, Mahasweta; Richards, Ryan M.; Biswas, Papu

doi:10.1016/j.micromeso.2019.04.034

Cited by 20 publications

(11 citation statements)

References 92 publications

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“…Many complexes of noble metals (Ru and Ir) 19 − 23 and transition metals (Mn, Pd, Cu, Ni, and Co) have been used as catalysts for the ADC reactions. 24 − 31 …”

Section: Introductionmentioning

confidence: 99%

Cucurbit[6]uril-Supported Fe₃O₄ Magnetic Nanoparticles Catalyzed Green and Sustainable Synthesis of 2-Substituted Benzimidazoles via Acceptorless Dehydrogenative Coupling

et al. 2022

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A new composite, cucurbit[6]uril (CB[6])-supported magnetic nanoparticles, Fe 3 O 4 –CB[6], was synthesized via a co-precipitation method in air and fully characterized by Fourier transform infrared spectroscopy, powder X-ray diffraction, X-ray photoelectron spectroscopy, field-emission scanning electron microscopy, high-resolution transmission electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, inductively coupled plasma–mass spectrometry, and vibrating sample magnetometry techniques. It has been found to be a highly efficient, economic, and sustainable heterogeneous catalyst and has been employed for the first time for the synthesis of a series of biologically important 2-substituted benzimidazoles from various benzyl alcohols and 1,2-diaminobenzenes under solvent-free conditions via acceptorless dehydrogenative coupling to afford the corresponding products in good to excellent yields (68–94%). The magnetic nature of the nanocomposite facilitates the facile recovery of the catalyst from the reaction mixture by an external magnet. The catalyst can be reused up to five times with negligible loss in its catalytic activity. All the isolated products were characterized by 1 H and 13 C{ 1 H} NMR spectroscopy.

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“…Many complexes of noble metals (Ru and Ir) 19 − 23 and transition metals (Mn, Pd, Cu, Ni, and Co) have been used as catalysts for the ADC reactions. 24 − 31 …”

Section: Introductionmentioning

confidence: 99%

Cucurbit[6]uril-Supported Fe₃O₄ Magnetic Nanoparticles Catalyzed Green and Sustainable Synthesis of 2-Substituted Benzimidazoles via Acceptorless Dehydrogenative Coupling

et al. 2022

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“…Thereafter, a further dehydrogenation step in the catalytic cycle resulted in intermediate IV , which involved an intramolecular proton transfer from alcohol to the metal‐bound hydride. Finally, the intermediate IV liberated molecular hydrogen to regenerate intermediate I to close the catalytic cycle [18a,37] . Theoretical calculations were performed to confirm the above proposed mechanism (Figure 5b; the structure of theoretical calculation models is displayed in Figures S8–S13).…”

Section: Resultsmentioning

confidence: 80%

Atomically Dispersed Co Clusters Anchored on N‐doped Carbon Nanotubes for Efficient Dehydrogenation of Alcohols and Subsequent Conversion to Carboxylic Acids

Fang

et al. 2021

ChemSusChem

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The catalytic dehydrogenation of readily available alcohols to high value‐added carbonyl compounds is a research hotspot with scientific significance. Most of the current research about this reaction is performed with noble metal‐based homogeneous catalysts of high price and poor reusability. Herein, highly dispersed Co‐cluster‐decorated N‐doped carbon nanotubes (Co/N‐CNTs) were fabricated via a facile strategy and used for the dehydrogenation of alcohols with high efficiency. Various characterization techniques confirmed the presence of metallic Co clusters with almost atomic dispersion, and the N‐doped carbon supports also enhanced the catalytic activity of Co clusters in the dehydrogenation reaction. Aldehydes as dehydrogenation products were further transformed in situ to carboxylic acids through a Cannizzaro‐type pathway under alkaline conditions. The reaction pathway of the dehydrogenation of alcohols was clearly confirmed by theoretical calculations. This work should provide an effective and simple approach for the accurate design and synthesis of small Co‐clusters catalysts for the efficient dehydrogenation‐based transformation of alcohols to carboxylic acids under mild reaction conditions.

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“…However, very few examples of effective heterogeneous catalysis through the acceptor-less dehydrogenative synthesis of benzoxazoles are known. Immobilized ruthenium complex catalyst 12) , as well as palladium oxide nanoparticles on mesoporous silica together with a large amount of strong base additive have been reported 27) . Therefore, development of solid, recyclable catalysts not requiring additives for this reaction would be very valuable.…”

Section: [Regular Paper]mentioning

confidence: 99%

Development of Titania-supported Iridium Catalysts for the Acceptor-less Dehydrogenative Synthesis of Benzoxazoles

Han

Wada

et al. 2021

J. Jpn. Petrol. Inst.

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Iridium catalysts supported on anatase with high surface area showed excellent activities for the acceptor-less dehydrogenation synthesis of benzoxazoles from 2-aminophenol and primary alcohols. The catalytic activity greatly depended on the titania supports, iridium precursors, and loading of iridium species. Catalysts supported on anatase JRC (Japan Reference Catalyst)-TIO-10 showed the highest activity for the dehydrogenative reaction. Preparation of catalysts using [Ir(cod)Cl]2 (cod 1,5-cyclooctadiene) as an iridium precursor resulted in higher activity than using Ir(acac)3 (acac acetylacetonate). Various primary alcohols were reacted to give corresponding benzoxazoles in high to moderate yields. The catalyst could be recycled without significant loss of activity, and no leaching of iridium species occurred into the solution. The hot filtration test strongly suggested that the catalysis occurs on the catalyst surface. Highly dispersed iridium species of less than 2 nm in diameter, which could be reduced at low temperature, were responsible for the excellent activity.

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Palladium oxide nanoparticles intercalated mesoporous silica for solvent free acceptorless dehydrogenation reactions of alcohols

Cited by 20 publications

References 92 publications

Cucurbit[6]uril-Supported Fe₃O₄ Magnetic Nanoparticles Catalyzed Green and Sustainable Synthesis of 2-Substituted Benzimidazoles via Acceptorless Dehydrogenative Coupling

Cucurbit[6]uril-Supported Fe₃O₄ Magnetic Nanoparticles Catalyzed Green and Sustainable Synthesis of 2-Substituted Benzimidazoles via Acceptorless Dehydrogenative Coupling

Atomically Dispersed Co Clusters Anchored on N‐doped Carbon Nanotubes for Efficient Dehydrogenation of Alcohols and Subsequent Conversion to Carboxylic Acids

Development of Titania-supported Iridium Catalysts for the Acceptor-less Dehydrogenative Synthesis of Benzoxazoles

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Palladium oxide nanoparticles intercalated mesoporous silica for solvent free acceptorless dehydrogenation reactions of alcohols

Cited by 20 publications

References 92 publications

Cucurbit[6]uril-Supported Fe3O4 Magnetic Nanoparticles Catalyzed Green and Sustainable Synthesis of 2-Substituted Benzimidazoles via Acceptorless Dehydrogenative Coupling

Cucurbit[6]uril-Supported Fe3O4 Magnetic Nanoparticles Catalyzed Green and Sustainable Synthesis of 2-Substituted Benzimidazoles via Acceptorless Dehydrogenative Coupling

Atomically Dispersed Co Clusters Anchored on N‐doped Carbon Nanotubes for Efficient Dehydrogenation of Alcohols and Subsequent Conversion to Carboxylic Acids

Development of Titania-supported Iridium Catalysts for the Acceptor-less Dehydrogenative Synthesis of Benzoxazoles

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Cucurbit[6]uril-Supported Fe₃O₄ Magnetic Nanoparticles Catalyzed Green and Sustainable Synthesis of 2-Substituted Benzimidazoles via Acceptorless Dehydrogenative Coupling

Cucurbit[6]uril-Supported Fe₃O₄ Magnetic Nanoparticles Catalyzed Green and Sustainable Synthesis of 2-Substituted Benzimidazoles via Acceptorless Dehydrogenative Coupling