General and selective reductive amination of carbonyl compounds using a core–shell structured Co<sub>3</sub>O<sub>4</sub>/NGr@C catalyst

Stemmler, Tobias; Westerhaus, Felix A.; Surkus, Annette‐Enrica; Pohl, Marga‐Martina; Junge, Kathrin; Beller, Matthias

doi:10.1039/c4gc00536h

Cited by 95 publications

(79 citation statements)

References 48 publications

(28 reference statements)

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“…Even though we have chosen toluene as our solvent, since it gave the best results under the optimized conditions, we investigated this effect in more detail. Contrary to previous work on reductions of nitro compounds,7a, 9 the use of aromatic solvents gave optimal results and the desired product is formed in 95 % yield.…”

Section: Methodscontrasting

confidence: 69%

Synthesis of Amines by Reductive Amination of Aldehydes and Ketones using Co₃O₄/NGr@C Catalyst

et al. 2014

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Heterogenized non‐noble metal‐based catalysts allow for cost‐efficient and environmentally benign hydrogenations. Here, we have developed a straightforward reductive amination methodology using molecular hydrogen in the presence of a Co3O4/NGr@C catalyst system. Various carbonyl compounds were transformed with secondary amines to the corresponding tertiary amines with good to excellent yields and selectivity. The Co3O4/NGr@C catalyst is recycled up to five times without significant loss of activity.

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Section: Methodscontrasting

confidence: 69%

Synthesis of Amines by Reductive Amination of Aldehydes and Ketones using Co₃O₄/NGr@C Catalyst

et al. 2014

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“…In the recent literature, methodologies for reductivea mination have been disclosed, which make use of expensive and rare metals such as Ru, Ir,P d, Pt, or Au as the catalyst. [13] In addition, Alonso et al employed nickel nanoparticles (NPs) as active catalytic speciesf or the reductive amination of aldehydes through transfer hydrogenation using isopropanol at mild temperatures. Beller et al already described the reductivea mination of aldehydesu sing nitroarenes as the nitrogen-containing compound in combination with ac arbonsupported iron-phenanthroline complex as the catalyst.…”

mentioning

confidence: 99%

Continuous Reductive Amination of Biomass‐Derived Molecules over Carbonized Filter Paper‐Supported FeNi Alloy

2015

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This paper reports the continuous reductive amination of different molecules, including biomass-related compounds, over carbon-supported FeNi nanoparticles obtained on the basis of inexpensive and abundant metal precursors and cellulose. A biorefinery case study for the preparation of pyrrolidones via acid-catalyzed hydrolysis of glucose followed by reductive amination of the obtained levulinic acid is described.

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“…Hence, merging rationally-designed suitable modified supports with cheap transition metals permits access to the design of active, selective and cheap catalytic materials thus allowing to match or to outperform noble-metal-based catalysts. During the last three years, some of us reported the preparation of active and selective NGr-decorated Co-based catalysts from the pyrolysis of in situ generated 1,10-phenanthroline (Phen) metal complexes using Vulcan® XC 72 R carbon [52][53][54][55][56][57][58][59][60], ceria [61] or α-alumina as supports [62]. Some of the obtained nanoscale catalysts exhibit a core-shell architecture in which a Co metallic core is enveloped by an oxidic sheath composed of Co3O4.…”

Section: Introductionmentioning

confidence: 99%

Co-based heterogeneous catalysts from well-defined α-diimine complexes: Discussing the role of nitrogen

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Ferretti

Topf

et al. 2017

Journal of Catalysis

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‡ These authors contributed equally to this work.Abstract: Ar-BIANs and related α-diimine Co complexes were wet impregnated onto Vulcan® XC 72 R carbon black powder and used as precursors for the synthesis of heterogeneous supported nanoscale catalysts by pyrolysis under argon at 800 °C. The catalytic materials feature a core-shell structure composed of metallic Co and Co oxides decorated with nitrogen-doped graphitic layers (NGr). These catalysts display high activity in the liquid phase hydrogenation of aromatic nitro compounds (110 °C, 50 bar H2) to give chemoselectively substituted aryl amines. The catalytic activity is closely related to the amount and type of nitrogen atoms in the final catalytic material, which suggests a heterolytic activation of dihydrogen.Keywords: cobalt, hydrogenation, nitro compounds, kinetic, heterolytic activation IntroductionCatalysis is a key-technology for the manufacturing of all kinds of bulk and fine chemical products. It allows for producing chemicals avoiding the formation of undesired and useless stoichiometric side products which leads to additional cost and energy consumption [1][2][3]. Many of the industrially relevant catalytic processes in the fine chemical industry are still based on expensive and rare late transition metals such as Pd, Pt, Rh, Ru and Ir [4,[1][2][3][4][5]. Although these metals exhibit very good catalytic performance for advanced organic substrates, the decreasing availability of these elements requires the development of efficient alternative metal-based catalysts [6]. In this regard, the design of catalytic systems based on abundant and biocompatible metals is an important goal for the implementation and progress of green and sustainable chemistry. Hence, transition metals such as Fe, Co and Cu are ideal candidates, which meet these requirements [7][8][9][10]. As a matter of fact, these elements are among the most abundant metals in the Earth's upper crust, thus being readily accessible [11]. Recently, heteroatom-doped carbon materials attracted major interest in the field of metal supported heterogeneous catalysts for both chemical synthesis [12][13][14] and/or energy-relevant transformations [15,16]. Indeed, doping graphene with heteroatoms such as N, B, P, or S leads to a radical modification of the electronic properties of both the support and the supported metal [17][18][19]. Consequently, it is possible to modify the activity and adjust the selectivity of the final catalytic material towards the desired transformation. Among the various dopants, nitrogen attracted most interest [15,[20][21][22]. and applications of transition metal/N-doped graphene (NGr) based catalytic systems ranges from oxygen reduction reactions (ORR) [23][24][25][26], hydrogen evolving reactions (HER) [27,28], photocatalysis [29,30], oxidation [31][32][33][34][35][36][37][38], and reduction [39][40][41][42][43][44] reactions of organic

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General and selective reductive amination of carbonyl compounds using a core–shell structured Co₃O₄/NGr@C catalyst

Cited by 95 publications

References 48 publications

Synthesis of Amines by Reductive Amination of Aldehydes and Ketones using Co₃O₄/NGr@C Catalyst

Synthesis of Amines by Reductive Amination of Aldehydes and Ketones using Co₃O₄/NGr@C Catalyst

Continuous Reductive Amination of Biomass‐Derived Molecules over Carbonized Filter Paper‐Supported FeNi Alloy

Co-based heterogeneous catalysts from well-defined α-diimine complexes: Discussing the role of nitrogen

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General and selective reductive amination of carbonyl compounds using a core–shell structured Co3O4/NGr@C catalyst

Cited by 95 publications

References 48 publications

Synthesis of Amines by Reductive Amination of Aldehydes and Ketones using Co3O4/NGr@C Catalyst

Synthesis of Amines by Reductive Amination of Aldehydes and Ketones using Co3O4/NGr@C Catalyst

Continuous Reductive Amination of Biomass‐Derived Molecules over Carbonized Filter Paper‐Supported FeNi Alloy

Co-based heterogeneous catalysts from well-defined α-diimine complexes: Discussing the role of nitrogen

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General and selective reductive amination of carbonyl compounds using a core–shell structured Co₃O₄/NGr@C catalyst

Synthesis of Amines by Reductive Amination of Aldehydes and Ketones using Co₃O₄/NGr@C Catalyst

Synthesis of Amines by Reductive Amination of Aldehydes and Ketones using Co₃O₄/NGr@C Catalyst