Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates

Casiello, Michele; Iannone, F.; Cotugno, Pietro; Monopoli, Antonio; Cioffi, Nicola; Ciminale, Francesco; Trzeciak, Anna M.; Nacci, Angelo

doi:10.1016/j.molcata.2015.06.007

Cited by 29 publications

(15 citation statements)

References 41 publications

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“…The latter eventually converts into the final product by intramolecular nucleophilic displacement, with the simultaneous elimination of hydrogen diselenide, which is oxidized back to elemental selenium by the action of oxygen (Scheme 12) [82]. More recently, the palladium-catalyzed oxidative carbonylation of simple ethylenediamine to imidazolidin-2-one (72% yield) (carried out in water at 100 • C with 1 mol% of palladium catalyst, under 40 atm of a CO/O 2 mixture [84]) was reported [85]. Scheme 12.…”

Section: Methodsmentioning

confidence: 99%

“…Moreover, in several cases, the use of a dehydrating agent is needed, because the water produced in the course of the process may negatively affect the product yield. However, the possibility of avoiding catalysts as well as organic solvents and other additives or promoters has also been demonstrated with simple aliphatic 1,2diamines, even though under rather harsh conditions (180 °C under 100 atm of CO2 for 24 h) [85].…”

Section: Methodsmentioning

confidence: 99%

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Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

et al. 2019

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2-Imidazolidinone and its analogues are omnipresent structural motifs of pharmaceuticals, natural products, chiral auxiliaries, and intermediates in organic syntheses. Over the years, continuous efforts have been addressed to the development of sustainable and more efficient protocols for the synthesis of these heterocycles. This review gives a summary of the catalytic strategies to access imidazolidin-2-ones and benzimidazolidin-2-ones that have appeared in the literature from 2010 to 2018. Particularly important contributions beyond the timespan will be mentioned. The review is organized in four main chapters that identify the most common approaches to imidazolidin-2-one derivatives: (1) the direct incorporation of the carbonyl group into 1,2-diamines, (2) the diamination of olefins, (3) the intramolecular hydroamination of linear urea derivatives and (4) aziridine ring expansion. Methods not included in this classification will be addressed in the miscellaneous section.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

et al. 2019

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“…With this in mind, in our ongoing efforts aimed at searching new green catalytic methods [ 33 , 34 , 35 , 36 , 37 , 38 ], we prepared a series of hybridized materials based on anatase and amine-grafted multiwalled carbon nanotubes (TiO 2 @amine-MWCNTs) and tested their ability to serve as an efficient catalyst for photoreduction of carbon dioxide.…”

Section: Introductionmentioning

confidence: 99%

TiO2@PEI-Grafted-MWCNTs Hybrids Nanocomposites Catalysts for CO2 Photoreduction

et al. 2018

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Anatase (TiO2) and multiwalled carbon nanotubes bearing polyethylenimine (PEI) anchored on their surface were hybridized in different proportions according to a sol-gel method. The resulting nanocomposites (TiO2@PEI-MWCNTs), characterized by BET, XRD, XPS, SEM, and UV techniques, were found efficient catalysts for CO2 photoreduction into formic and acetic acids in water suspension and under visible light irradiation. PEI-grafted nanotubes co-catalysts are believed to act as CO2 activators by forming a carbamate intermediate allowing to accomplish the first example in the literature of polyamines/nanotubes/TiO2 mediated CO2 photoreduction to carboxylic acids.

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“…The reaction is performed in the presence of a metal catalyst or organocatalyst, an oxidizing agent such as I 2 or O 2 /air, and CO pressure. Among transition metals and organocatalysts, Mn, Pd,– Cu, Au,– Co,– W– Ni, Rh, Ru, S, and Se are effective. Usually, a non‐nucleophilic solvent is required to avoid the formation of carbamates .…”

Section: Introductionmentioning

confidence: 99%

Selective Oxidative Carbonylation of Aniline to Diphenylurea with Ionic Liquids

et al. 2018

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A catalytic system for the selective oxidative carbonylation of aniline to diphenylurea based on Pd complexes in combination with imidazolium ionic liquids is presented. Both oxidants, Pd complexes, and ionic liquids affect the activity of the reaction, and the choice of oxidant determines the selectivity of the reaction. Together they allow the reaction to proceed under comparatively mild conditions without a loss of activity. Examination of the reaction by use of in situ NMR spectroscopy allowed us to observe an intermediate suggested only previously, which supported the proposed mechanism.

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Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates

Cited by 29 publications

References 41 publications

Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

TiO2@PEI-Grafted-MWCNTs Hybrids Nanocomposites Catalysts for CO2 Photoreduction

Selective Oxidative Carbonylation of Aniline to Diphenylurea with Ionic Liquids

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