Oriana Piermatti

Università degli Studi di Perugia | UNIPG · Department of Chemistry Biology and Biotechnology

The direct functionalization of an inactivated C–H bond has become an attractive approach to evolve toward step-economy, atom-efficient and environmentally sustainable processes. In this regard, the design and preparation of highly active metal nanoparticles as efficient catalysts for C–H bond activation under mild reaction conditions still continu...

Among transition metal nanoparticles, palladium nanoparticles (PdNPs) are recognized for their high catalytic activity in a wide range of organic transformations that are of academic and industrial importance. The increased interest in environmental issues has led to the development of various green approaches for the preparation of efficient, low-...

The design of highly active metal nanoparticles to be employed as efficient heterogeneous catalysts is a key tool for the construction of complex organic molecules and the minimization of their environmental costs. The formation of novel C–N bonds via C–H activation is an effective atom-economical strategy to access high value materials in pharmace...

Herein, we report the use of nontoxic, water-miscible Polarclean as a safe dipolar aprotic solvent for the metal-catalyzed direct C2–H arylation of indoles using Pd/C as a catalyst. The developed method allows reaching excellent yields and regioselectivities, and it tolerates various substituents on both indole and diaryliodonium salt scaffolds. Po...

Herein, we disclose the first C–2-selective C–H alkenylation of quinoline N–oxides catalyzed by a heterogeneous palladium catalyst. The protocol does not require the use of an external oxidant and it is applicable to an ample substrates scope always showing excellent site selectivity. This process is made accessible by the use of a specific 1,2,3-t...

A resin-bound 1,2,4-triazolium ionic tag has been used as support for the preparation of solid palladium nanoparticles (Pd(0)-POLI-TAG-Pd). Owing to the pincer-type architecture of the triazolium ligand, the stabilization of a high amount of palladium nanoparticles (16 wt%) has been possible. The catalytic system has been fully characterized and us...

Herein we report the use of Rhodiasolv© Polarclean as a novel polar aprotic solvent for the synthesis of decorated heterocycles via dipolar cycloaddition (isooxazoles) or intramolecular C–H functionalization processes (benzo-fused chromenes). The use of Polarclean allowed to isolate the final products in good yields by simple solid filtration or li...

A gold‐incorporated SBA‐15 catalyst was prepared by a solvent‐free ball‐milling approach. The catalyst showed high reactivity and selectivity in the reduction of a variety of nitroarenes to anilines operating in absolute EtOH with NaBH4 as reducing agent. The catalyst was reused in batch conditions over five consecutive runs without any losses of a...

In the present paper, a novel inorgano-organic layered material, a zirconium phosphate aminoethyl phosphonate, ZP(AEP), bearing aminoethyl groups on the layer surface, was used to immobilize AuNPs by a two step procedure. The gold-based catalyst, Au1@ZP(AEP), containing 1 wt% Au, was characterized in terms of physico-chemical properties and TEM ana...

The hydroamination of alkynes is a straightforward and atom-economical process for the synthesis of substituted nitrogen-containing alkenes. Herein we report a novel protocol that involves for the first time solvent-free conditions (SolFC) and the use of an organic base, namely 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosph...

Three different basic zirconium potassium phosphate methyl and/or phenyl phosphonates of general formula Zr(PO3OK)2-(x+y)(PO3Me)x(PO3Ph)y namely ZrKP-Me, ZrKP-Ph and ZrKP-MePh have been prepared as amorphous solids. The catalytic activity of the solids was tested in the Knoevenagel condensation between several aldehydes with malononitrile and ethyl...

We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines. Furfuryl alcohol (FA) can be used in mixture with water to form the corresponding azeotrope (20%wt of FA) and therefore can be easily recovered and...

Biomass-derived levulinic acid (LA) is an excellent substrate to obtain high-value esters that can be used as second-generation biofuels and biofuel additives. The present study focuses on the identification and definition of the key parameters crucial for the development of chemically and environmentally efficient protocols operating in continuous...

Zirconium phosphate glycine diphosphonate nanosheets (ZPGly) have been used as support for the preparation of solid palladium nanoparticles, namely Pd@ZPGly. Thanks to the presence of carboxy-aminophosponate groups on the layer surface, ZPGly-based materials were able to stabilize a high amount of palladium (up to 22 wt %) also minimizing the amoun...

Green/Sustainable Chemistry is the scientific platform where chemists are contributing from different areas to develop modern and efficient processes aimed at minimizing the environmental impact of chemical production. To reach these goals scientists, from both academia and industry, need to strongly focus their fundamental and innovative research...

This review summarizes recent contributions on the use of fluoride catalysts immobilized on polymer supports. Besides the commercially available Amberlyst fluoride, TBAF on silica gel, and TBAF on alumina, that have proved widely useful for several interesting and valuable synthetic C–N, C–O, and C–C bond transformations, novel catalysts based on t...

The protocol uses Amberlite IRA 900 F as the catalyst and allows the isolation of pure β-cyanoketones without any purification except in the case of (VIIb) and (IXa).

Thin nanosheets from a layered zirconium phosphate-carboxyphosphonate is reported here. Small Pd nanoparticles have been supported on these nanosheets by an efficient method. The resulting Pd-catalyst was fully characterized and tested in the Suzuki-Miyaura coupling. The catalytic system proved its efficiency as it was reused for several cycles and...

We report herein a clean multistep flow process that starting from α,β-unsaturated ketones 1 allows the preparation of N-Boc-γ-amino alcohols 3 in high yields. The final products have been isolated in pure form without any additional purification step. The cleanness and environmental efficiency achieved using our protocol are proven by the calculat...

Palladium nanoparticles on layered potassium α-zirconium phosphate (PdNP/α-ZrPK) with high palladium loading (10.6 wt%) have been prepared and used as catalyst in low amount (0.1 mol% of Pd) in the Heck reaction of methyl acrylate and styrene with a series of aryl iodides in CH3CN/H2O azeotrope as a green medium. The procedure has been optimized un...

An efficient protocol for the synthesis of beta-amino acids starting from easily accessible alpha,beta-unsaturated carboxylic acids based on the combination of two heterogeneous catalytic systems is reported. This multistep approach is based on the direct beta-azidation of alpha,beta-unsaturated carboxylic acids and subsequent azido group reduction...

γ-Valerolactone (GVL) can be a valid biobased replacement for toxic dipolar aprotic solvents especially in widely used cross-coupling reactions. In this contribution, we have proved that GVL can be a useful medium for the Hiyama reaction, and we developed a practical and efficient protocol for the Hiyama coupling using a nonexpensive and commercial...

A clean and efficient protocol for the synthesis of a wide variety of N-Boc-beta-amino ketones 3a-g has been defined using flow approach. The multistep procedure is based on the beta-azidation of unsaturated ketones, consecutive reduction of the azido group, and concomitant amino group protection, and furnishes the desired products in good yields a...

Stable L-proline-functionalized zirconium methyl- and/or phenylphosphonates have been prepared as amorphous solids by the precipitation of (4R)-4-[(4′-phosphonobenzyl)oxy]-L-proline and methyl- and/or phenylphosphonic acid with ZrOCl2. The supported L-proline catalysts were tested in the direct asymmetric aldol addition between several ketones and...

Optimized conditions allow the direct synthesis of title compounds from Danishefsky′s diene and N-benzylideneanilines.

There is much chemistry between water and epoxide. This contribution deals with the use of water in processes based on the epoxide ring opening. Reported examples highlight the role of water not as a simple substitution of the organic medium or as an exotic option to claim the greenness of a process, but also show the role of this medium for reachi...

a b s t r a c t Zirconium phosphates methyl and/or phenyl phosphonates-supported L-proline have been prepared as amorphous solids by precipitation of (4R)-4-(phosphonooxy)-L-proline, methyl and/or phenyl phos-phonic acid with ZrOCl 2 . The supported L-proline catalysts were tested on the direct asymmetric aldol addition of cyclohexanone to p-nitrob...

New zirconium hydrogen phosphate alkyl and/or aryl phosphonates of general formula Zr(PO3OH)2−(x+y)(PO3R)x(PO3R1)y have been prepared as amorphous solids. The presence of hydrophobic groups such as Me, Ph and Pr and their percentage have an important role in the definition of the corresponding solid structure. All the prepared solids are micro- and...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The aza-Diels–Alder reaction between benzaldimines 1 and Danishefsky's diene in solvent-free conditions is reported for the first time. The reaction occurs rapidly at 30°C and is catalyzed by porous α-zirconium hydrogen phosphate (p-αZrP) in the presence of sodium dodecyl sulfate (SDS). The yields were excellent. The recycling of the catalyst has a...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

High-pressure Diels-Alder reactions of various alkoxy/alkyl-substituted benzylideneacetones with methyl-1,3-butadienes are reported. Activation by high pressure (8-11 kbar) in combination with the mild Lewis acid HfCl(4).2THF allows these reactions to efficiently and regioselectively produce a series of ortho-substituted cyclohexenyl-benzene cycloa...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The aldol reaction is one of the most important ways to construct carbon-carbon bonds in organic synthesis. Nature itself seems to prefer this reaction in its biosynthetic processes, for example, in the prebiotic formation of saccharides [1]. Strictly speaking, the aldol reaction is the self-coupling of an aldehyde, having at least one active hydro...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The condensation reactions of acetophenone, cyclohexanone, isophorone, phenylacetonitrile, p-nitrophenylacetonitrile, (phenylsulfonyl)acetonitrile and indene with benzaldehyde were studied in water in heterogeneous phase in the presence and absence of anionic and cationic surfactants such as SLS, CTACl, (CTA)2SO4 and CTAOH. All the reactions occur...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Diels-Alder cycloaddition reactions of 3-cyanocoumarin, hydroxy-substituted 3-cyanocoumarins and mesyl-substituted 3-cyano-coumarins with methyl-1,3-butadienes carried out under high pressure (11 kbar) are reported. Activation by high pressure allows these reactions to proceed satisfactorily under mild conditions to produce 6a-cyano-hydroxy- and 6a...

The direct aza-Diels–Alder reaction between 2-cyclohexen-1-one (1) and benzaldimines 2 in water is reported for the first time. The reaction occurs at 30 °C, is catalyzed by layered α-zirconium hydrogen phosphate (α-ZrP) and requires the presence of sodium dodecyl sulfate (SDS). The reaction yield is excellent, the reaction is faster and the exo di...

Nitric oxide (NO) acts as an autacoid molecule that diffuses from its endothelial production site to the neighboring muscular cells. NO-donors are often used to mimic the physiological effects of NO in biological systems. Organic nitrates are commonly used as NO-donors; the most popular, glycerol trinitrate (GTN), has been used in therapy for more...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Several α-Zr[O3PC6H4SO2NHCH(CH(CH3)2)COOH)]2−x(O3PCH3)x·nH2O samples, containing chiral pendent groups, were prepared by allowing Zr fluoro complexes to decompose in the presence of N-(m-solfophenyl)-l(+)-Valine-phosphonic (PVal) and methanphosphonic (PMe) acids. The layered compounds were characterized by different techniques and left to react wit...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

An innovative route to prepare a number of variously substituted new biphenyl derivatives is presented here. The protocol avoids the use of a catalyst, an organic solvent, and dry conditions. [reaction: see text]

[reaction: see text] Diels-Alder reactions of 3-substituted coumarins 1a-g with methyl-1,3-butadienes 2a-c carried out in water alone and in CH2Cl2 under 9 kbar pressure are reported. In aqueous medium satisfactory results were obtained by operating at 150 degrees C, whereas under high pressure the cycloadditions were complete at 60-70 degrees C wi...

TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-cyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glas...

The synthesis of 7-hydroxy-3-carboxycoumarin in water is discussed. The experiment is suitable for an undergraduate-level organic chemistry lab course. Performing this type of synthesis the students may begin to appreciate two advantages of using an aqueous medium in organic synthesis, that is, being able to perform several reactions in sequence si...

For Abstract see ChemInform Abstract in Full Text.

The [4 + 2] cycloadditions of 3-nitrocoumarin (1a), 6-chloro-3-nitrocoumarin (1b), and 6-, 7-, and 8-hydroxy-3-nitrocoumarins (1c, 5, and 6) with (E)-piperylene (7), isoprene (8), 2,3-dimethyl-1,3-butadiene (9), 2-methoxy-1,3-butadiene (10), 2,3-dimethoxy-1,3-butadiene (11), and cyclopentadiene (12) were investigated in aqueous medium, in organic s...

The use of indium salts as catalysts and mediators in addition, cyclization, aromatic electrophilic substitution, nucleophilic substitution, coupling, reduction, rearrangement and polymerization reactions that have appeared in papers published between 2000 and the first half of 2002 is reviewed. InCl3, InBr3, InI3, InCl, InBr, InI, In(OTf)3, and In...

Buy Article Permissions and Reprints Abstract Chloro-, hydroxy-, methoxy-, and tert-butyl-substituted 3-carboxycoumarins have been prepared by one-pot procedure by reaction of suitably substituted salicylaldehydes with malononitrile in water. The over-all yields are high and the protocol does not require organic solvents. Key words aldol reaction...

Nucleophilic ring opening of 1,2-epoxides in aqueous medium in the presence and absence of metal salts is reviewed. Azidolysis, hydrolysis, iodolysis and thiolysis are the reactions mainly investigated. The pH of the reaction medium controls the reactivity and regioselectivity of the process. By working at suitable pH values, even salts such as AlC...

(+)-(R)-[2.2]Paracyclophane[4,5-d]-1,3-oxazol-2(3H)-one exhibiting planar chirality has been used as a chiral auxiliary in asymmetric Diels-Alder, Michael, and aldol reactions of alpha,beta-unsaturated carboxy and enolate imides, respectively. The endo-exo- and face-diastereoselectivity is good and is controlled by the spatial relationship between...

Novel planar chiral N,O-ligands derived from (R)-(+)and (S)-(-)-2,4-dimethyl[2]paracyclo[2](5,8)quinolinophane were synthesized and employed as catalyst in the enantioselective addition of diethylzine to aromatic aldehydes. On the basis of the ee values, ranging from 30% to 75%, and the configuration of the obtained 1-phenyl-1-propanols a plausible...

(+)-(R)-[2.2]Paracyclophane[4,5-d]-1,3-oxazol-2(3H)-one exhibiting planar chirality has been used as a chiral auxiliary in asymmetric Diels-Alder, Michael, and aldol reactions of alpha,beta-unsaturated carboxy and enolate imides, respectively. The endo-exo- and face- diastereoselectivity is good and is controlled by the spatial relationship between...

The Knoevenagel addition of aryl aldehydes 1 with nitroacetonitrile 2 in water followed by dehydration of β-nitroalcohols 3, allows (E)-2-aryl-1-cyano-1-nitroethenes 4 to be prepared by a one-pot procedure without using organic solvents. The reuse of the aqueous medium makes this process inexpensive and highly environmentally friendly. The protocol...

The [4 + 2] cycloadditions of (E)-2-aryl-1-cyano-1-nitroalkenes 1 with achiral and enantiopure vinyl ethers 2 and 3 carried out in sole water are reported. These reactions occur in a heterogeneous phase under mild conditions and are fast and highly stereoselective. By using (-)-N,N-dicyclohexyl-(1S)-isoborneol-10-sulfonamide as a chiral auxiliary,...

The cycloadditions of (E)-3-diazenylbut-2-enes 1 with a variety of alkenes 2 – 6 were carried out in water as well as in organic solvents. The reactions were always faster in heterogeneous aqueous medium than in the organic solvents. These conjugated diazenyl-alkenes behave mainly as heterodienes, and the Diels-Alder adducts are the sole or at leas...

Recently the aqueous medium has attracted the interest of organic chemists, and many, sometimes surprising, discoveries have been made. Among the organic reactions investigated in aqueous medium, the Diels−Alder cycloaddition has been the most widely studied because of its great importance in the synthetic and theoretical fields. The Diels−Alder re...

Recently the aqueous medium has attracted the interest of organic chemists, and many, sometimes surprising, discoveries have been made. Among the organic reactions investigated in aqueous medium, the Diels−Alder cycloaddition has been the most widely studied because of its great importance in the synthetic and theoretical fields. The Diels−Alder re...

The cycloadditions of (E)-3-diazenylbut-2-enes 1 with a variety of alkenes 2-6 were carried out in water as well as in organic solvents. The reactions were always faster in heterogeneous aqueous medium than in the organic solvents. These conjugated diazenyl-alkenes behave mainly as heterodienes and the Diels-Alder adducts are the sole or at least m...

The synthesis of optically active (+)-(R)-[2.2]paracyclophano[4,5-d]-oxazol-2(3H)-one is described. The aldol reaction of N-acyl derivatives of this planar chiral auxiliary with beazaldehyde occurs with good diastereo- and enantioselectivity.

The synthesis and reactivity in aqueous medium of compounds having the 2- and 4-pyrone subunits (pyronoids) are reviewed. The results obtained in aqueous medium are compared with those carried out in organic solvent.

The CD spectra of a new series of 4-substituted [2.2]paracyclophanes 1b–e have been measured down to 185 nm. Polarizability calculations within the DeVoe model satisfactorily reproduce the CD features over all the spectral range. In addition, the analysis of the complete CD spectrum allowed a phenomenological interpretation of the dependence of the...

Oxidation of organic compounds has probably been the most widely investigated process because it is of interest to both academic scientists and industrial technicians. Many oxidants and catalysts are known and a number of reaction conditions have been carefully investigated [1], The modern chemical industry requires selective highly efficient oxida...

The enzymatic kinetic resolution of (±)-4-acetoxy[2.2]paracyclophane by Candida cylindracea lipase was investigated in water and in a two-phase aqueous organic system. The (+)-(R)-4-hydroxy- and (+)-(S)-4-acetoxy[2.2]-paracyclophanes were isolated in excellent yields and high enantiomeric excesses. The resolution was carried out on multi-gram scale...

(R)-4-Hydroxy-, -4-fluoro-, -4-bromo-, and -4-iodo[2.2]paracyclophanes have been prepared and their absolute configuration assigned on the basis of chemical correlations. Different relationships between the specific optical rotation and the group polarizability have been found depending on the ability of the substituents to conjugate with the aroma...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

3-Cyanocoumarin and seven derivatives [4-Me; 6-NO2; 7-OH; 7-OMe; 8-OH; 5,7-OMe; 6,7-(-CH=CH-)-2] and eight coumarins substituted at C-3 (CO2Et; NO2; Ph; p-NO2-C6H4; Ph-SO2; 2-pyridyl; 2-thienyl; 2-benzothiazolyl) were prepared, on multigram scale by a one-pot procedure in water alone, by the Knoevenagel reaction of o-hydroxyaryl aldehydes and o-hyd...

The aldol-type addition of chiral boron enolates of (methylthio)acetic acid to various aldehydes gives α-(methylthio)-β-hydroxy acids stereoselectively and with good yields. The desulfenylation of methyl esters of the condensation adducts allows methyl esters of α-unsubstituted β-hydroxy acids to be obtained with high ee. Derivatives of (+)-2- and...

The organic functional groups, formyl, cyano, hydroxymethyl and methylsulfenyl, are oxidized with high yields in water only by using TBHP and controlling the pH of the reaction medium. In the presence of (CTA)2SO4, the oxidation of the easily oxidizable sulfide group is prevented and a highly chemoselective process is obtained. The role of the surf...