Reduction of CX to CH2 by Wolff–Kishner and Other Hydrazone Methods

Hutchins, Robert O.; Hutchins, MaryGail K.

doi:10.1016/b978-0-08-052349-1.00230-4

Cited by 52 publications

(19 citation statements)

References 185 publications

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“…This behaviour is in contrast to most of the deoxygenation catalysts previously reported, which tend to lose their activity due to the accumulation of water. 5a,16 The possibility to recycle the Fe 25 Ru 75 @SILP catalyst was studied using 4 0 -hydroxyacetophenone (1) as substrate. Fully constant conversion and selectivity towards the formation of 4-ethylphenol (1c) were obtained in five consecutive runs without any make-up or regeneration (Fig.…”

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confidence: 99%

Selective hydrodeoxygenation of hydroxyacetophenones to ethyl-substituted phenol derivatives using a FeRu@SILP catalyst

et al. 2020

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confidence: 99%

Selective hydrodeoxygenation of hydroxyacetophenones to ethyl-substituted phenol derivatives using a FeRu@SILP catalyst

et al. 2020

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“…Many chemical solvents involved in synthetic organic reactions are not friendly to the environment. For instance, Wolff-Kishner reduction reactions typically use a solvent system that is comprised of ethylene glycol or diethylene glycol (DEG) (15). DEG has been observed in rat models to be metabolized in the liver into a hydrogen ion, NADH, and 2-hydroxyethoxyacetaldehyde.…”

Section: Introductionmentioning

confidence: 99%

Wolff–Kishner reduction reactions using a solar irradiation heat source and a green solvent system

Agee¹,

Mullins²,

Biernacki³

et al. 2014

Green Chemistry Letters and Reviews

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“…This provides access to a broad range of ethylphenol derivatives that are important building blocks for the production of fine chemicals, polymers, and pharmaceuticals. 60 , 61 …”

Section: Discussionmentioning

confidence: 99%

Metal Nanoparticles Immobilized on Molecularly Modified Surfaces: Versatile Catalytic Systems for Controlled Hydrogenation and Hydrogenolysis

Bordet

Leitner

2021

Acc. Chem. Res.

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Conspectus The synthesis and use of supported metal nanoparticle catalysts have a long-standing tradition in catalysis, typically associated with the field of heterogeneous catalysis. More recently, the development and understanding of catalytic systems composed of metal nanoparticles (NPs) that are synthesized from organometallic precursors on molecularly modified surfaces (MMSs) have opened a conceptually new approach to the design of multifunctional catalysts (NPs@MMS). These complex yet fascinating materials bridge molecular (“homogeneous”) and material (“heterogeneous”) approaches to catalysis and provide access to catalytic systems with tailor-made reactivity through judicious combinations of supports, molecular modifiers, and nanoparticle precursors. A particularly promising field of application is the controlled activation and transfer of dihydrogen, enabling highly selective hydrogenation and hydrogenolysis reactions as relevant for the conversion of biogenic feedstocks and platform chemicals as well as for novel synthetic pathways to fine chemicals and even pharmaceuticals. Consequently, the topic offers an emerging field for interdisciplinary research activities involving organometallic chemists, material scientists, synthetic organic chemists, and catalysis experts. This Account will provide a brief overview of the historical background and cover examples from the most recent developments in the field. A coherent account on the methodological and experimental basis will be given from the long-standing experience in our laboratories. MMSs are widely accessible via chemisorption and physisorption methods for the generation of stable molecular environments on solid surfaces, whereby a special emphasis is given here to ionic liquid-type molecules as modifiers (supported ionic liquid phases, SILPs) and silica as support material. Metal nanoparticles are synthesized following an organometallic approach, allowing the controlled formation of small and uniformly dispersed monometallic or multimetallic NPs in defined composition. A combination of techniques from molecular and material characterization provides a detailed insight into the structure of the resulting materials across various scales (electron microscopy, solid-state NMR, XPS, XAS, etc.). The molecular functionalities grafted on the silica surface have a pronounced influence on the formation, stabilization, and reactivity of the NPs. The complementary and synergistic fine-tuning of the metal and its molecular environment in NPs@MMSs allow in particular the control of the activation of hydrogen and its transfer to substrates. Monometallic (Ru, Rh, Pd) monofunctional NPs@MMSs possess excellent activities for the hydrogenation of alkenes, alkynes, and arenes for which a nonpolarized (homolytic) activation of H 2 is predominant. The incorporation of 3d metals in noble metal NPs to give bimetallic (FeRu, CoRh, etc.) monofunctional NPs@MMSs favors a more polarized H 2 ...

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Reduction of CX to CH2 by Wolff–Kishner and Other Hydrazone Methods

Cited by 52 publications

References 185 publications

Selective hydrodeoxygenation of hydroxyacetophenones to ethyl-substituted phenol derivatives using a FeRu@SILP catalyst

Selective hydrodeoxygenation of hydroxyacetophenones to ethyl-substituted phenol derivatives using a FeRu@SILP catalyst

Wolff–Kishner reduction reactions using a solar irradiation heat source and a green solvent system

Metal Nanoparticles Immobilized on Molecularly Modified Surfaces: Versatile Catalytic Systems for Controlled Hydrogenation and Hydrogenolysis

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