Catalytic activation of hydrazine hydrate by gold nanoparticles: Chemoselective reduction of nitro compounds into amines

Gkizis, Petros; Stratakis, Manolis; Lykakis, Ioannis N.

doi:10.1016/j.catcom.2013.02.024

Cited by 101 publications

(59 citation statements)

References 37 publications

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“…During the process for the reduction of 6, four typical methods utilizing hydrazine hydrate [14][15][16], iron powder [17,18], zinc dust [19][20][21] and palladium [22][23][24] were screened (Table 3). At the initial stage, reduction of 6 with hydrazine hydrate was incapable of thoroughly converting nitro to amino, along with the The optimization results were estimated by detecting the purity of the next-step product 7 and the two- An efficient and high-yielding protocol for the production… formation of impurities 7e and 7f (Fig.…”

Section: Resultsmentioning

confidence: 99%

An efficient and high-yielding protocol for the production of Regorafenib via a new synthetic strategy

Wang

Zuo

et al. 2015

Res Chem Intermed

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An improved, high-yielding, and efficient protocol for the production of Regorafenib (1), a novel diaryl urea inhibitor of multiple protein kinases, is described. The highlight of the process chemistry design and development is an optimization of the route for preparing key intermediate 4-(4-amino-3-fluorophenoxy)-N-methylpicolinamide (7) by O-alkylation, nitration and reduction reactions. The developed process avoids using column chromatography to isolate 7, reduces the reaction requirements and is cost-saving, resulting in an increased overall yield from 35.0 to 57.0 % and purity from 97.0 to 99.8 %.

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Section: Resultsmentioning

confidence: 99%

An efficient and high-yielding protocol for the production of Regorafenib via a new synthetic strategy

Wang

Zuo

et al. 2015

Res Chem Intermed

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“…On the other hand, 4-AP is an important intermediate for the production of pharmaceuticals substances, photographic materials and rubber materials. [21] Since the reduction of the nitro group into an amine is an important process, in this study, we focus on the application of biosynthesised AuNPs for the reduction of 4-NP to 4-AP with the presence of excess hydrazine hydrate as reductant.…”

Section: Introductionmentioning

confidence: 99%

Biostabilised icosahedral gold nanoparticles: synthesis, cyclic voltammetric studies and catalytic activity towards 4-nitrophenol reduction

Borhamdin

Shamsuddin

Alizadeh

2015

Journal of Experimental Nanoscience

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A green and cost-effective biosynthetic approach for the preparation of icosahedral gold nanoparticles (AuNPs) using an aqueous leaf extract of Polygonum minus as reducing and stabilising factor is described. The reduction of Au 3C ions to elemental Au rapidly occurred and is completed within 20 minutes at room temperature. The size of the nanoparticles is highly sensitive to the AuCl 4 ¡ /leaf extract concentration ratio and pH. Transmission electron microscopy and X-ray diffraction data indicated that the nanoparticles were in a crystalline shape (face-centred cubic), mostly icosahedral and nearly monodispersed with an average size of 23 nm. Cyclic voltammetric studies suggested that flavonoids, such as quercetin and myricetin present in the leaf extract had a tendency to donate electrons to Au 3C ions and the formation of elemental Au was possible due to the transfer of electrons from these flavonoids to Au 3C ions. Infrared absorption of the AuNPs and the leaf extract revealed that the oxidised (quinone) form of quercetin and myricetin were presumably the main stabilising agents in the formation of stable nanoparticles. The present biosynthesis of AuNPs was simple, rapid, cost-effective and environmentally friendly. The newly prepared biostabilised icosahedral AuNPs show good catalytic activity in the reduction of 4-nitrophenol (4-NP) to 4-aminophenol (4-AP).

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“…Issues of sustainable production and safe handling are now drivers for alternative sources of hydrogen and/or hydrogen donors. Several hydrogen carriers including hydrazine [3], ammonia-borane complexes [4], esters [5], alcohols [6] and acids [7] have been employed in homogeneous and heterogeneous transfer hydrogenation but application is hampered due to the required separation steps for catalyst reuse. A continuous heterogeneous catalytic system that combines dehydrogenation with hydrogen release that is utilised in hydrogenation represents an alternative approach that circumvents the requirement for an external hydrogen supply.…”

Section: Introductionmentioning

confidence: 99%

‘‘Hydrogen-Free’’ Hydrogenation of Nitrobenzene Over Cu/SiO2 Via Coupling with 2-Butanol Dehydrogenation

Hao

Cárdenas‐Lizana

et al. 2014

Top Catal

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The feasibility of a coupled reaction system for the simultaneous production of 2-butanone (from 2-butanol dehydrogenation) and aniline (from nitrobenzene hydrogenation) over Cu/SiO 2 in continuous gas phase operation without an external H 2 supply has been established. Two (15.9 and 1.8 % w/w) Cu/SiO 2 catalysts were prepared by deposition-precipitation and characterised in terms of N 2 physisorption, temperature programmed reduction (TPR), H 2 chemisorption, powder XRD, STEM and XPS analysis. Following TPR, the higher Cu loading showed a wider particle size distribution (1-15 nm, mean 7.8 nm) than 1.8 % w/w Cu/SiO 2 (1-6 nm, mean 3.1 nm), where the latter exhibited a modified electronic character based on XPS measurements and a (fourfold) higher H 2 uptake capacity. The reactions showed antipathetic (dehydrogenation) and sympathetic (hydrogenation) structure sensitivity in terms of turnover frequency (TOF) dependence on Cu size. We have achieved, for the first time, 100 % yield to both target products (2-butanone and aniline) with appreciably (by a factor of 50) enhanced hydrogen utilisation in the coupled system relative to conventional nitrobenzene reduction using pressurised H 2 . Our results establish in situ hydrogen generation via catalytic dehydrogenation as a viable hydrogenation route to commercially important products.

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Catalytic activation of hydrazine hydrate by gold nanoparticles: Chemoselective reduction of nitro compounds into amines

Cited by 101 publications

References 37 publications

An efficient and high-yielding protocol for the production of Regorafenib via a new synthetic strategy

An efficient and high-yielding protocol for the production of Regorafenib via a new synthetic strategy

Biostabilised icosahedral gold nanoparticles: synthesis, cyclic voltammetric studies and catalytic activity towards 4-nitrophenol reduction

‘‘Hydrogen-Free’’ Hydrogenation of Nitrobenzene Over Cu/SiO2 Via Coupling with 2-Butanol Dehydrogenation

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