Aerobic oxidation of hydroxylamines with nanoporous gold catalyst as an efficient synthetic method of nitrones

S, Salprima Yudha; Kusuma, Indra; Asao, Naoki

doi:10.1016/j.tet.2015.05.094

Cited by 15 publications

(5 citation statements)

References 72 publications

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“…The oxidation of nitrogen-containing organic molecules is often difficult to perform in a selective fashion because a variety of products and intermediates may be involved starting from the amine to the highest oxidation state: hydroxylamines, nitrones, oximes, nitroso compounds, and nitro compounds as well as N–N coupled products such as hydrazines, diazocompounds, and azoxycompounds. Therefore, the selective oxidation of hydroxylamines to the nitrones can be regarded as a breakthrough in this regard (Scheme D) …”

Section: Catalysis By Nanoporous Gold In Organic Synthesismentioning

confidence: 99%

“…Therefore, the selective oxidation of hydroxylamines to the nitrones can be regarded as a breakthrough in this regard (Scheme 2D). 618 A more unusual oxidation reaction that is one of the very few applied reactions is the oxidative dealkylation or cyclization of lidocaine, which was performed to synthesize a drug metabolite (Scheme 2E). 619 This reaction can yield two products, depending entirely on the reaction conditions, but in a selective fashion.…”

Section: Oxidation Reactions Of Organic Molecules By Nanoporous Goldmentioning

confidence: 99%

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Nanoporous Gold: From Structure Evolution to Functional Properties in Catalysis and Electrochemistry

et al. 2023

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Nanoporous gold (NPG) is characterized by a bicontinuous network of nanometer-sized metallic struts and interconnected pores formed spontaneously by oxidative dissolution of the less noble element from gold alloys. The resulting material exhibits decent catalytic activity for low-temperature, aerobic total as well as partial oxidation reactions, the oxidative coupling of methanol to methyl formate being the prototypical example. This review not only provides a critical discussion of ways to tune the morphology and composition of this material and its implication for catalysis and electrocatalysis, but will also exemplarily review the current mechanistic understanding of the partial oxidation of methanol using information from quantum chemical studies, model studies on single-crystal surfaces, gas phase catalysis, aerobic liquid phase oxidation, and electrocatalysis. In this respect, a particular focus will be on mechanistic aspects not well understood, yet. Apart from the mechanistic aspects of catalysis, best practice examples with respect to material preparation and characterization will be discussed. These can improve the reproducibility of the materials property such as the catalytic activity and selectivity as well as the scope of reactions being identified as the main challenges for a broader application of NPG in target-oriented organic synthesis.

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Section: Catalysis By Nanoporous Gold In Organic Synthesismentioning

confidence: 99%

Section: Oxidation Reactions Of Organic Molecules By Nanoporous Goldmentioning

confidence: 99%

Nanoporous Gold: From Structure Evolution to Functional Properties in Catalysis and Electrochemistry

et al. 2023

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“…The catalytic oxidation was reported by Murahashi and co-workers for the first time with palladium black catalyst in 1983 . The aerobic oxidation can be catalyzed by gold nanoparticles supported on silica (Au/SiO 2 ) or unsupported nanoporous gold (AuNPore) highly efficiently. Similarly, rhodium nanoparticles supported on carbon nanotube (Rh/CNT) catalyze the aerobic oxidation of hydroxylamines .…”

Section: Synthesis Of Nitronesmentioning

confidence: 99%

Synthesis and Transformations of Nitrones for Organic Synthesis

2019

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Nitrones are important compounds and are highly useful in many aspects. The first part describes the methods for synthesis of nitrones, which are useful and environmentally friendly. Catalytic oxidations, condensations, and other useful reactions are described. The nitrones thus obtained are key intermediates for the synthesis of biologically important nitrogen compounds. The second part describes the fundamental transformations of nitrones, which will provide the strategies and means for the construction of nitrogen compounds. The reactions with nucleophiles or radicals, C–H functionalization, and various addition reactions are described. The last reactions are particularly important for highly selective carboncarbon bond formations. 1,3-Dipolar cycloaddition reactions are excluded because the size of the review is limited and excellent reviews have been published in Chemical Reviews.

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“…In summary, the results in Table disclose how Ru 2 (OAc) 4 Cl (1 mol %) catalyst is able to afford the aerobic oxidation of a wide range of N , N ‐hydroxylamines to nitrones in water, the best sustainable solvent. This result is remarkable, also considering that the few existing aerobic procedures for this transformation are scarcely reproducible, use nongreen solvents or employ higher amounts (5–10 mol %) of gold‐based heterogenous catalysts in MeOH as solvent ,…”

Section: Figurementioning

confidence: 99%

Diruthenium Diacetate Catalysed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilisation to Lysozyme

et al. 2017

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Some of us recentlyr eportedt he synthesis and structuralc haracterisation of am ixed-valence diruthenium adduct of lysozyme, ([HEWL/Ru 2 (OAc) 2 ], hereafter) originating from its direct reactionw ith the lantern-like complex diruthenium tetraacetate chloride,u nder physiological-likec onditions. [1] Interestingly,c ombined electrospray ionisation mass spectrometry (ESI-MS) and X-ray diffraction studies revealed that the binding of the [Ru 2 (m-O 2 CCH 3 ) 2 -(H 2 O) 2 ] 3 + fragment occurs selectively in two different sites, at the level of two exposed aspartate groups,a cting as bidentate ligands for the ruthenium atoms ( Figure 1). We were intriguedb yt he possible use of [HEWL/Ru 2 (OAc) 2 ] in catalysis and speculated that the persistence of the intact diruthenium motif would guarantee preservation of the interesting and peculiar catalytic properties exhibitedb y Ru 2 (OAc) 4 Cl. This latter complex showed significant catalytic properties, particularly in redox processes, either as ac atalyst

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Aerobic oxidation of hydroxylamines with nanoporous gold catalyst as an efficient synthetic method of nitrones

Cited by 15 publications

References 72 publications

Nanoporous Gold: From Structure Evolution to Functional Properties in Catalysis and Electrochemistry

Nanoporous Gold: From Structure Evolution to Functional Properties in Catalysis and Electrochemistry

Synthesis and Transformations of Nitrones for Organic Synthesis

Diruthenium Diacetate Catalysed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilisation to Lysozyme

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