Cerium(IV) Ammonium Nitrate as a Catalyst in Organic Synthesis

Sridharan, Vellaisamy; Menéndez, J. Carlos

doi:10.1021/cr100004p

Cited by 255 publications

(130 citation statements)

References 204 publications

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“…Cerium salts have moderate cost and are available commercially [4]. Ce(IV) has numerous applications as a prepared reagent, for instance, ammonium cerium(IV) nitrate is used in many organic synthesis reactions involving oxidation as well as Brønsted and Lewis acid catalysis [5]. Binnemans has published a comprehensive review of the application Ce(IV) compounds [6], discussing their use as versatile reagents for a myriad of organic reactions due to their ability to promote radical reactions, functionalize alkenes and catalyse esterifications.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical redox processes involving soluble cerium species

Arenas

León

Walsh

2016

Electrochimica Acta

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Anodic oxidation of cerous ions and cathodic reduction of ceric ions, in aqueous acidic solutions, play an important role in electrochemical processes at laboratory and industrial scale. Ceric ions, which have been used for oxidation of organic wastes and off-gases in environmental treatment, are a wellestablished oxidant for indirect organic synthesis and specialised cleaning processes, including oxide film removal from tanks and process pipework in nuclear decontamination. They also provide a classical reagent for chemical analysis in the laboratory. The reversible oxidation of cerous ions is an important reaction in the positive compartment of various redox flow batteries during charge and discharge cycling. A knowledge of the thermodynamics and kinetics of the redox reaction is critical to an understanding of the role of cerium redox species in these applications. Suitable choices of electrode material (metal or ceramic; coated or uncoated), geometry/structure (2-or 3-dimensional) and electrolyte flow conditions (hence an acceptable mass transport rate) are critical to achieving effective electrocatalysis, a high performance and a long lifetime. This review considers the electrochemistry of soluble cerium species and their diverse uses in electrochemical technology, especially for redox flow batteries and mediated electrochemical oxidation.

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Section: Introductionmentioning

confidence: 99%

Electrochemical redox processes involving soluble cerium species

Arenas

León

Walsh

2016

Electrochimica Acta

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“…Because of the experience acquired by our group in the use of cerium(IV) ammonium nitrate ((NH 4 ) 2 Ce(NO 3 ) 6 ,C AN) as ac atalyst, [31] we started our study by examining the reaction between butylamine, ethyl acetoacetate, and 4-chlorophenacyl bromide in the presence of CAN. In spite of the fact that Hantzsch pyrrole syntheses described in the literature are normally regioselective, our reactiona lways afforded mixtureso f the two possible regioisomeric pyrroles, namely 1h and 2.…”

Section: Resultsmentioning

confidence: 99%

Three‐Component Synthesis of Pyrrole‐Related Nitrogen Heterocycles by a Hantzsch‐Type Process: Comparison between Conventional and High‐Speed Vibration Milling Conditions

et al. 2016

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The use of solvent-free, high-speed vibration milling conditions has allowed the development of ao ne-pot telescoped process for the synthesis of pyrroles starting from ketones, primary amines, and b-dicarbonyl compounds and comprising an initial a-iodination followed by an in situ three-component Hantzsch-type reaction. This methodw as compared with as olution-based protocol from a-iodoketones, primary amines,a nd b-dicarbonyl compounds. Although both protocols were far more general than previous Hantzsch-type pyrrole syntheses, the mechanochemical methodw as superior in that it afforded considerably higher yields in spite of comprising an additional step. The stereochemicali ntegrity of the pyrroles obtained from chiral aaminoesters wasm aintained. This solvent-free method was also used for the efficient preparationo fter-a nd quater-aryl/ heteroaryl frameworks containing two pyrrole units and avariety of fused pyrrole systems, including benzo[g]indoles, indeno[1,2-b]pyrroles, indoles,and homoindoles.

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“…C NMR spectra were measured in CDCl3 or DMSO-d6 on a 250 or 400 MHz Brüker spectrometer. 1 H chemical shifts are reported in ppm from an internal standard TMS, residual chloroform (7.26 ppm) or DMSO-d6 (2.50 ppm). 13 C NMR chemical shifts are reported in ppm from an internal standard TMS, residual chloroform (77.16 ppm) or DMSO-d6 (39.43 ppm).…”

Section: Methodsmentioning

confidence: 99%

“…Reactions of CAN include, oxidation, oxidative addition, oxidative catalysis, nitration, photo-oxidation, carbon-carbon and carbon-heteroatom bond formation, carbon-carbon, carbon-heteroatom and Si-O bond cleavage, fragmentation, alkoxylation, esterification and transesterification, dehydrogenation, catalysis of multicomponent syntheses and polymer grafting, as described in recent review articles. 1,2 CAN has played a significant role in oxidative cyclisations giving access to various heterocycles, although the synthesis of five-membered rings with two heteroatoms is limited to benzimidazoles, 3 pyrazoles, 4 benzothiazoles 5,6 and isoxazoles. 7 CAN has been reported to cleave semicarbazones to the corresponding aldehydes and ketones 8 but hydrazones are not affected.…”

Section: Introductionmentioning

confidence: 99%

Cerium(IV) ammonium nitrate for the tandem nitration and oxidative rearrangement of 2-acetyl-1-naphthol benzoylhydrazones into 1,2-diacylnaphthalenes; synthesis of benzo[f]phthalazines

Tzinavou¹,

Dolka²,

Tsoungas³

et al. 2017

Arkivoc

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A novel nitration and oxidation reaction sequence of 2-acetyl-1-naphthol benzoylhydrazones with CAN is presented. There is strong indication that nitration precedes an oxidative rearrangement to 1,2-diacyl-4-nitronaphthalenes or oxidative electrocyclisation to 3-methyl-5-nitronaphtho[2,1-d]isoxazole. Condensation of 1,2-diacyl-4-nitronaphthalenes with hydrazine hydrate yields 1,4-disubstituted benzo[f]phthalazines.

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Cerium(IV) Ammonium Nitrate as a Catalyst in Organic Synthesis

Cited by 255 publications

References 204 publications

Electrochemical redox processes involving soluble cerium species

Electrochemical redox processes involving soluble cerium species

Three‐Component Synthesis of Pyrrole‐Related Nitrogen Heterocycles by a Hantzsch‐Type Process: Comparison between Conventional and High‐Speed Vibration Milling Conditions

Cerium(IV) ammonium nitrate for the tandem nitration and oxidative rearrangement of 2-acetyl-1-naphthol benzoylhydrazones into 1,2-diacylnaphthalenes; synthesis of benzo[f]phthalazines

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