Co-SAC catalyzed utilization of methanol and ethanol in the transfer hydrogenation of azo bonds: experimental and theoretical studies

Panja, Dibyajyoti; Dey, Sadhan; Saha, Rohini; Sahu, Rajib; Das, Gourab Kanti; Bhobe, Preeti; Kundu, Sabuj

doi:10.1039/d3gc02725b

Cited by 5 publications

(4 citation statements)

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“…However, the process is challenging owing to the inferior reactivity and lower bond polarity of the azo double bond. 8 Moreover, overreduction of azoarenes can yield unwanted amine derivatives, 9 emphasizing the need for an efficient, selective semihydrogenation method.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Among various methods of preparing hydrazaorenes, catalytic semihydrogenation of azoarenes is considered the most general and direct method for synthesizing hydrazoarenes. However, the process is challenging owing to the inferior reactivity and lower bond polarity of the azo double bond . Moreover, over-reduction of azoarenes can yield unwanted amine derivatives, emphasizing the need for an efficient, selective semihydrogenation method.…”

Section: Introductionmentioning

confidence: 99%

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In Situ Generated Bimetallic Nanoparticle Catalysts for the Transfer Semihydrogenation of Azoarenes

Park,

Kim,

Han

2024

ACS Sustainable Chem. Eng.

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Hydrazoarenes are important structural components extensively utilized across diverse industries, such as dyes and pharmaceuticals; they are also vital in supramolecular chemistry for the synthesis of highly substituted aniline derivatives. Although the semihydrogenation of azoarenes is a common method for hydrazoarene synthesis, developing an efficient and selective semihydrogenation method remains challenging. Bimetallic nanoparticle catalysts present a promising avenue for enhancing these hydrogenation reactions through the synergistic effects of two metals, potentially enhancing the catalytic activity or selectivity. However, determining the optimal metal combination for maximizing the synergistic effects in azoarene semihydrogenation poses a significant challenge. In this study, we present an innovative approach for in situ generation of bimetallic nanoparticle catalysts for the transfer semihydrogenation of azoarenes. This method involves the straightforward generation of bimetallic nanoparticles by adding ammonia borane (NH 3 BH 3 ) to an ethanol solution containing two metal salts. Among the various bimetallic catalysts investigated, NiZn (a combination of Ni and Zn salts) exhibited the highest activity and selectivity for the semihydrogenation reaction, enabling the selective reduction of various azoarenes to their corresponding hydrazoarenes under mild reaction conditions. The proposed method offers an efficient catalytic system for the transfer semihydrogenation of azoarenes.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In Situ Generated Bimetallic Nanoparticle Catalysts for the Transfer Semihydrogenation of Azoarenes

Park,

Kim,

Han

2024

ACS Sustainable Chem. Eng.

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“…Recently, nitrogen-doped carbon (NC) supported catalysts have attained immense interest in electrocatalysis and organic transformation reactions because of their tunable electronic properties, structural flexibility, and porosity. 12,13 In this context, we and other groups have investigated the use of metal–organic framework (MOF)-derived MN x @NC catalysts for electrocatalytic energy conversion and catalytic organic reactions. 14,15…”

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confidence: 99%

“…17,18 The strong interaction between the metal centers and the NC-support minimizes the particle agglomeration and increases the catalyst stability. 13 Although MN x @NC for different organic reactions has been explored, the MOF-derived catalysts are rarely studied. 11 Only recently, NiN 4 @NC, Co@NC, Fe@NC, etc.…”

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confidence: 99%

The low loading of metal in metal–organic framework-derived NiN_x@NC promotes amide formation through C–N coupling

Vyas,

Kumar,

Indra

2024

Chem. Commun.

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Transfer Hydrogenative Cleavage of N═N Bond of Azoarenes to Aminoarenes Using Ruthenium Catalyst

Mohanty,

Sinha,

Kenguva

et al. 2024

ChemCatChem

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Textile industry contaminants cause significant pollution of water resources, making them a major worry in the modern age. Azo dyes, one of the most harmful synthetic colours generated in textile industry pollutants, are particularly persistent in water bodies due to their chemical composition. Herein, an efficient transfer hydrogenative cleavage of ‐N=N‐ moiety containing azoarene to its corresponding aminoarene is accomplished using a terpyridine‐based Ruthenium complex. This report depicts the suitable transformations from the azoarene by adopting a minimal base and catalyst loading. The preliminary mechanistic studies disclosed the selective conversion of azoarene to its complete ‐N=N‐ cleavage product aminoarenes through the hydrazoarene intermediate.

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Co-SAC catalyzed utilization of methanol and ethanol in the transfer hydrogenation of azo bonds: experimental and theoretical studies

Abstract: Transfer hydrogenation (TH) of non-polar bonds using methanol and ethanol as hydrogen source is a great challenge, and development of efficient 3d metal-based catalyst to accomplish such reactions is an...

Cited by 5 publications

References 95 publications

In Situ Generated Bimetallic Nanoparticle Catalysts for the Transfer Semihydrogenation of Azoarenes

In Situ Generated Bimetallic Nanoparticle Catalysts for the Transfer Semihydrogenation of Azoarenes

The low loading of metal in metal–organic framework-derived NiN_x@NC promotes amide formation through C–N coupling

Transfer Hydrogenative Cleavage of N═N Bond of Azoarenes to Aminoarenes Using Ruthenium Catalyst

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Co-SAC catalyzed utilization of methanol and ethanol in the transfer hydrogenation of azo bonds: experimental and theoretical studies

Abstract: Transfer hydrogenation (TH) of non-polar bonds using methanol and ethanol as hydrogen source is a great challenge, and development of efficient 3d metal-based catalyst to accomplish such reactions is an...

Cited by 5 publications

References 95 publications

In Situ Generated Bimetallic Nanoparticle Catalysts for the Transfer Semihydrogenation of Azoarenes

In Situ Generated Bimetallic Nanoparticle Catalysts for the Transfer Semihydrogenation of Azoarenes

The low loading of metal in metal–organic framework-derived NiNx@NC promotes amide formation through C–N coupling

Transfer Hydrogenative Cleavage of N═N Bond of Azoarenes to Aminoarenes Using Ruthenium Catalyst

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The low loading of metal in metal–organic framework-derived NiN_x@NC promotes amide formation through C–N coupling