Chemoselective Hydrogenation of Functionalized Nitroarenes using Supported Mo Promoted Pt Nanoparticles

Boymans, Evert; Boland, Susan; Witte, Peter T.; Müller, Christian; Vogt, Dieter

doi:10.1002/cctc.201200437

Cited by 49 publications

(47 citation statements)

References 9 publications

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“…The interaction between Rh and α-FeOOH, as confirmed by XPS above, may also contribute to the improvement of catalytic activity. The effect of temperature on catalytic performance was very remarkable, and the reaction becomes slower as the temperature decreased (entries [8][9][10][11]. Therefore, the optimum reaction conditions were fixed.…”

Section: Full Papermentioning

confidence: 99%

“…[3,8] However, the selective reduction of the nitro group of nitrostyrenes is a particular challenge because the hydrogenation of vinyl group is thermodynamically prior. Many technologies have been reported so far to improve selectivity, including the addition of appropriate additives, [9] modification of active metals, [10] adjustment of the metal-support interaction, [11] and use of relatively inert metal catalysts. [12] However, these approaches have more or less defects, such as inconvenient preparation and too long reaction time, or sacrificing activity to improve selectivity, which are not satisfactory in practical production.…”

Section: Introductionmentioning

confidence: 99%

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Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

Liu

et al. 2019

Adv Synth Catal

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Control of chemoselectivity is a special challenge for the reduction of nitroarenes bearing one or more unsaturated groups. Here, we report a flower‐like Rh/α‐FeOOH catalyst for the chemoselective hydrogenation of nitrostyrene to vinylaniline over full conversion, which benefits the new functionalized aminostyrene because the multisubstituted aminostyrenes are usually commercially unavailable. This catalyst does not only show desirable selectivity for the vinylanilines, but also exhibits the inertness to various other reducible groups over wide reaction duration. The catalytic selectivity for the reduction of the nitro group towards vinyl group was investigated by the control experiments and FT‐IR analysis. We have found that the abundant hydroxyl groups in the α‐FeOOH may contribute to the improvement of catalytic activity and selectivity. Furthermore, the catalyst exhibits excellent stability and keeps its catalytic performance even after 6 cycles.

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Section: Full Papermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

Liu

et al. 2019

Adv Synth Catal

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“…[1,3] Generally,p referential activation of the nitro group can be promoted by modifying the platinum-group metal with other metals.F or example,aR hIn/SiO 2 catalyst showed good catalytic performance under mild conditions. [5,6] But the use of harmful modifiers would be detrimental to sustainable chemistry. Moreover,p referential activation of the nitro group could also be promoted by the addition of phosphorous additives.…”

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confidence: 99%

ZnAl‐Hydrotalcite‐Supported Au₂₅ Nanoclusters as Precatalysts for Chemoselective Hydrogenation of 3‐Nitrostyrene

et al. 2017

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Chemoselective hydrogenation of 3-nitrostyrene to 3-vinylaniline is quite challenging because of competitive activation of the vinyl group and the nitro group over most supported precious-metal catalysts. A precatalyst comprised of thiolated Au nanoclusters supported on ZnAl-hydrotalcite yielded gold catalysts of a well-controlled size (ca. 2.0 nm)-even after calcination at 500 °C. The catalyst showed excellent selectivity (>98 %) with respect to 3-vinylaniline, and complete conversion of 3-nitrostyrene over broad reaction duration and temperature windows. This result is unprecedented for gold catalysts. In contrast to traditional catalysts, the gold catalyst is inert with respect to the vinyl group and is only active with regard to the nitro group, as demonstrated by the results of the control experiments and attenuated total reflection infrared spectra. The findings may extend to design of gold catalysts with excellent chemoselectivity for use in the synthesis of fine chemicals.

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“…This result is consistent with the high activity previously observed in hydrogenation reactions using NanoSelect catalysts 6. 7 The Al 2 O 3 ‐supported Pt(HHDMA) is also the most active, which led to 99 % conversion in 30 min.…”

Section: Resultsmentioning

confidence: 99%

NanoSelect Precious Metal Catalysts and their Use in Asymmetric Heterogeneous Catalysis

Kirby¹,

Moreno‐Marrodán

Baan

et al. 2014

ChemCatChem

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We studied the surface modification of supported colloidal precious metal catalysts. Chiral compounds derived from cinchona alkaloids and prolinol were synthesized and used as stabilizers/reductants to yield Pd and Pt colloidal nanoparticles. The new Pd catalysts were found to be highly active and selective catalysts for the semihydrogenation of 3‐hexyn‐1‐ol to cis‐3‐hexen‐1‐ol. The stabilizers affected the activity of the catalyst but not the selectivity. The catalysts were also evaluated in the asymmetric hydrogenation of methyl pyruvate and isophorone. No enantioselectivity was observed, which indicated that surface modification by the stabilizer did not induce chirality in the substrate. Achiral supported Pd and Pt colloidal catalysts were modified with cinchonidine. The modified Pt catalysts demonstrated a high activity for the hydrogenation of methyl pyruvate and a modest enantioselectivity of 47 %, which indicated that the chiral induction of supported colloidal catalysts is possible by modifying the catalyst surface with a chiral reagent.

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Chemoselective Hydrogenation of Functionalized Nitroarenes using Supported Mo Promoted Pt Nanoparticles

Cited by 49 publications

References 9 publications

Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

ZnAl‐Hydrotalcite‐Supported Au₂₅ Nanoclusters as Precatalysts for Chemoselective Hydrogenation of 3‐Nitrostyrene

NanoSelect Precious Metal Catalysts and their Use in Asymmetric Heterogeneous Catalysis

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Chemoselective Hydrogenation of Functionalized Nitroarenes using Supported Mo Promoted Pt Nanoparticles

Cited by 49 publications

References 9 publications

Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

ZnAl‐Hydrotalcite‐Supported Au25 Nanoclusters as Precatalysts for Chemoselective Hydrogenation of 3‐Nitrostyrene

NanoSelect Precious Metal Catalysts and their Use in Asymmetric Heterogeneous Catalysis

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ZnAl‐Hydrotalcite‐Supported Au₂₅ Nanoclusters as Precatalysts for Chemoselective Hydrogenation of 3‐Nitrostyrene