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Fabio Aricò
Department of Environmental Sciences, Informatics and Statistics, Ca’ Foscari University of Venice, 30172 Venezia, Italy

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Journal article
Published: 13 August 2021 in Sustainable Chemistry
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Commercially available Purolite CT151 demonstrated to be an efficient acid catalyst for the synthesis of alkyl levulinates via alcoholysis of furfuryl alcohol (FA) at mild temperatures (80–120 °C) and short reaction time (5 h). Reaction conditions were first optimized for the synthesis of ethyl levulinate and then tested for the preparation of methyl-, propyl-, isopropyl-, butyl, sec-butyl- and allyl levulinate. Preliminary scale-up tests were carried out for most of the alkyl levulinates (starting from 5.0 g of FA) and the resulting products were isolated as pure by distillation in good yields (up to 63%). Furthermore, recycling experiments, conducted for the preparation of ethyl levulinate, showed that both the Purolite CT151 and the exceeding ethanol can be recovered and reused for four consecutive runs without any noticeable loss in the catalyst activity.

ACS Style

Mattia Annatelli; Giacomo Trapasso; Lucrezia Lena; Fabio Aricò. Alkyl Levulinates from Furfuryl Alcohol Using CT151 Purolite as Heterogenous Catalyst: Optimization, Purification, and Recycling. Sustainable Chemistry 2021, 2, 493 -505.

AMA Style

Mattia Annatelli, Giacomo Trapasso, Lucrezia Lena, Fabio Aricò. Alkyl Levulinates from Furfuryl Alcohol Using CT151 Purolite as Heterogenous Catalyst: Optimization, Purification, and Recycling. Sustainable Chemistry. 2021; 2 (3):493-505.

Chicago/Turabian Style

Mattia Annatelli; Giacomo Trapasso; Lucrezia Lena; Fabio Aricò. 2021. "Alkyl Levulinates from Furfuryl Alcohol Using CT151 Purolite as Heterogenous Catalyst: Optimization, Purification, and Recycling." Sustainable Chemistry 2, no. 3: 493-505.

Cover picture
Published: 20 May 2021 in European Journal of Organic Chemistry
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The Front Cover shows the one-pot procedure for the introduction of aminoalkyl chain through dialkyl carbonate chemistry into different phenolic substrates. This green approach is a direct alcohol substitution that avoids the use of chlorine chemistry giving CO2 and ethanol as the only reaction by-products. The proposed procedure has numerous potential applications as N,N-dialkyl ethylamine moieties are incorporated in many pharmacophore scaffolds such as Tamoxifen, Raloxifene, Amiodarone, Phenyltoloxamine and Trifenagrel. The authors thank Thomas Bassano for creating the artwork. More information can be found in the Communication by F. Aricò et al.

ACS Style

Mattia Annatelli; Giacomo Trapasso; Claudio Salaris; Cristiano Salata; Sabrina Castellano; Fabio Aricò. Front Cover: Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols (24/2021). European Journal of Organic Chemistry 2021, 2021, 3458 -3458.

AMA Style

Mattia Annatelli, Giacomo Trapasso, Claudio Salaris, Cristiano Salata, Sabrina Castellano, Fabio Aricò. Front Cover: Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols (24/2021). European Journal of Organic Chemistry. 2021; 2021 (24):3458-3458.

Chicago/Turabian Style

Mattia Annatelli; Giacomo Trapasso; Claudio Salaris; Cristiano Salata; Sabrina Castellano; Fabio Aricò. 2021. "Front Cover: Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols (24/2021)." European Journal of Organic Chemistry 2021, no. 24: 3458-3458.

Communication
Published: 26 April 2021 in European Journal of Organic Chemistry
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N,N ‐dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts and especially pharmaceuticals. Common synthetic procedures for its the incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Herein is reported a one‐pot synthetic approach for the easy introduction of aminoalkyl chain via dialkyl carbonate (β‐aminocarbonate) chemistry into different phenolic substrates. This new direct alcohol substitution procedure avoids the use of chlorine chemistry, is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β‐aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.

ACS Style

Mattia Annatelli; Giacomo Trapasso; Claudio Salaris; Cristiano Salata; Sabrina Castellano; Fabio Arico'. Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols. European Journal of Organic Chemistry 2021, 2021, 3459 -3464.

AMA Style

Mattia Annatelli, Giacomo Trapasso, Claudio Salaris, Cristiano Salata, Sabrina Castellano, Fabio Arico'. Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols. European Journal of Organic Chemistry. 2021; 2021 (24):3459-3464.

Chicago/Turabian Style

Mattia Annatelli; Giacomo Trapasso; Claudio Salaris; Cristiano Salata; Sabrina Castellano; Fabio Arico'. 2021. "Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols." European Journal of Organic Chemistry 2021, no. 24: 3459-3464.

Paper
Published: 06 April 2021 in Catalysis Science & Technology
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High-yielding methylation of isosorbide via DMC chemistry promoted by N-methyl pyrrolidine is herein reported. This study addresses: DMI purification, scale-up tests, insights on the catalyst role and on the reaction pathways leading to DMI.

ACS Style

Mattia Annatelli; Davide Dalla Torre; Manuele Musolino; Fabio Aricò. Dimethyl isosorbide via organocatalyst N-methyl pyrrolidine: scaling up, purification and concurrent reaction pathways. Catalysis Science & Technology 2021, 11, 3411 -3421.

AMA Style

Mattia Annatelli, Davide Dalla Torre, Manuele Musolino, Fabio Aricò. Dimethyl isosorbide via organocatalyst N-methyl pyrrolidine: scaling up, purification and concurrent reaction pathways. Catalysis Science & Technology. 2021; 11 (10):3411-3421.

Chicago/Turabian Style

Mattia Annatelli; Davide Dalla Torre; Manuele Musolino; Fabio Aricò. 2021. "Dimethyl isosorbide via organocatalyst N-methyl pyrrolidine: scaling up, purification and concurrent reaction pathways." Catalysis Science & Technology 11, no. 10: 3411-3421.

Journal article
Published: 08 February 2021 in Pure and Applied Chemistry
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Biorefinery is defined as a sustainable process where biomass is converted in a spectrum of marketable products and fuels. In this view, C6 furan-based compounds, usually referred as furanics, have been extensively investigated as aromatic promising building blocks from renewables. 5-Hydroxymethylfurfural (HMF) and 2,5-furan dicarboxylic acid (FDCA) are well known examples of furanics whose syntheses and applications have been extensively reviewed in the literature. Herein for the first time it is reported a comprehensive overview on the synthetic procedures to another bio-derived furan compounds, i.e. 2,5-bis(hydroxymethyl)furan (BHMF), a stable bio-based diol with numerous applications as monomer for bio-materials and fuels. Advantages and limitations of the different synthetic approaches are addressed, as well as possible future developments to render this compound part of the biorefinery market.

ACS Style

Fabio Aricò. Synthetic approaches to 2,5-bis(hydroxymethyl)furan (BHMF): a stable bio-based diol. Pure and Applied Chemistry 2021, 93, 551 -560.

AMA Style

Fabio Aricò. Synthetic approaches to 2,5-bis(hydroxymethyl)furan (BHMF): a stable bio-based diol. Pure and Applied Chemistry. 2021; 93 (5):551-560.

Chicago/Turabian Style

Fabio Aricò. 2021. "Synthetic approaches to 2,5-bis(hydroxymethyl)furan (BHMF): a stable bio-based diol." Pure and Applied Chemistry 93, no. 5: 551-560.

Short communication
Published: 23 December 2020 in Sustainable Chemistry and Pharmacy
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Several alkyl carbonate derivatives of 5-hydroxymethylfurfural (HMF) and 2,5-bis(hydroxymethyl)furan (BHMF) have been synthesized for the first time. In most cases high yields were achieved using mild reaction conditions and compounds were recovered as pure with none or minimal purification. The new HMF and BHMF derived products resulted stable over time and they are suitable monomers for new bio-based polycarbonates and polyurethanes.

ACS Style

Angel Gabriel Sathicq; Mattia Annatelli; Iskandar Abdullah; Gustavo Romanelli; Fabio Aricò. Alkyl carbonate derivatives of furanics: A family of bio-based stable compounds. Sustainable Chemistry and Pharmacy 2020, 19, 100352 .

AMA Style

Angel Gabriel Sathicq, Mattia Annatelli, Iskandar Abdullah, Gustavo Romanelli, Fabio Aricò. Alkyl carbonate derivatives of furanics: A family of bio-based stable compounds. Sustainable Chemistry and Pharmacy. 2020; 19 ():100352.

Chicago/Turabian Style

Angel Gabriel Sathicq; Mattia Annatelli; Iskandar Abdullah; Gustavo Romanelli; Fabio Aricò. 2020. "Alkyl carbonate derivatives of furanics: A family of bio-based stable compounds." Sustainable Chemistry and Pharmacy 19, no. : 100352.

Review article
Published: 12 February 2020 in Current Opinion in Green and Sustainable Chemistry
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D-sorbitol and isosorbide have been indicated by US Department of Energy (DOE) among the 15 target molecules of special interest for biorefinery development. This minireview reports on isosorbide conversion into potential substitutes of petrochemicals. In the last two years, investigations on the peculiar reactivity of isosorbide have been focused on preparation of green solvents, bio-based monomers for polymerization reactions, functional materials, synthesis of pharmaceuticals, surfactants, novel organocatalysts, potential flame retardants and crosslinking agents.

ACS Style

Fabio Aricò. Isosorbide as biobased platform chemical: Recent advances. Current Opinion in Green and Sustainable Chemistry 2020, 21, 82 -88.

AMA Style

Fabio Aricò. Isosorbide as biobased platform chemical: Recent advances. Current Opinion in Green and Sustainable Chemistry. 2020; 21 ():82-88.

Chicago/Turabian Style

Fabio Aricò. 2020. "Isosorbide as biobased platform chemical: Recent advances." Current Opinion in Green and Sustainable Chemistry 21, no. : 82-88.

Editorial
Published: 12 February 2020 in Frontiers in Chemistry
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Editorial: Green Synthesis of Heterocycles

ACS Style

Fabio Aricò. Editorial: Green Synthesis of Heterocycles. Frontiers in Chemistry 2020, 8, 1 .

AMA Style

Fabio Aricò. Editorial: Green Synthesis of Heterocycles. Frontiers in Chemistry. 2020; 8 ():1.

Chicago/Turabian Style

Fabio Aricò. 2020. "Editorial: Green Synthesis of Heterocycles." Frontiers in Chemistry 8, no. : 1.

Editorial
Published: 27 December 2019 in Current Opinion in Green and Sustainable Chemistry
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ACS Style

Fabio Aricò; Ramon Moreno Tost. Editorial Overview: Editorial: Toward new sustainable development goals. Current Opinion in Green and Sustainable Chemistry 2019, 21, A1 -A3.

AMA Style

Fabio Aricò, Ramon Moreno Tost. Editorial Overview: Editorial: Toward new sustainable development goals. Current Opinion in Green and Sustainable Chemistry. 2019; 21 ():A1-A3.

Chicago/Turabian Style

Fabio Aricò; Ramon Moreno Tost. 2019. "Editorial Overview: Editorial: Toward new sustainable development goals." Current Opinion in Green and Sustainable Chemistry 21, no. : A1-A3.

Journal article
Published: 10 December 2019 in Sustainable Chemistry and Pharmacy
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Keggin-type heteropolyacids have been used as catalyst for the selective oxidation of olefins to the corresponding epoxides in multiphase conditions (isooctane/Aliquat 336/water). Multiphase system allowed achieving a higher conversion (72%) and selectivity (70%) to epoxide than the corresponding homogeneous or biphasic systems in the presence of the same catalyst. Optimization of the multiphase system has been conducted considering reaction time, temperature, amount of the catalysts and quantity of the oxidant. The best-found reaction conditions were then employed for the selective epoxidation of several substrates. Interestingly, it was shown that, in the multiphase system, only an insignificant decomposition of hydrogen peroxide was observed. Furthermore, an environmental assessment has been conducted comparing green metrics related to the homogenous, biphasic and multiphase systems herein investigated.

ACS Style

Ángel G. Sathicq; Luis R. Pizzio; Patricia G. Vázquez; Pietro Tundo; Fabio Aricò; Gustavo P. Romanelli. Keggin heteropolyacid as catalyst for olefin epoxidation: A multiphase approach. Sustainable Chemistry and Pharmacy 2019, 15, 100201 .

AMA Style

Ángel G. Sathicq, Luis R. Pizzio, Patricia G. Vázquez, Pietro Tundo, Fabio Aricò, Gustavo P. Romanelli. Keggin heteropolyacid as catalyst for olefin epoxidation: A multiphase approach. Sustainable Chemistry and Pharmacy. 2019; 15 ():100201.

Chicago/Turabian Style

Ángel G. Sathicq; Luis R. Pizzio; Patricia G. Vázquez; Pietro Tundo; Fabio Aricò; Gustavo P. Romanelli. 2019. "Keggin heteropolyacid as catalyst for olefin epoxidation: A multiphase approach." Sustainable Chemistry and Pharmacy 15, no. : 100201.

Research article
Published: 25 November 2019 in ACS Sustainable Chemistry & Engineering
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Dimethyl isosorbide (DMI) – a well-known bio-based high boiling green solvent – was used, for the first time in the preparation of Poly(vinylidene fluoride)- and Polyethersulfone-based membranes. Preliminary thermodynamic (Hansen and Hildebrand solubility parameters, relative energy difference) and kinetic (viscosity) studies on DMI confirmed that this solvent possesses the required physical/chemical properties to be exploited in casting membrane. Membranes were prepared by non-solvent induced phase separation (NIPS) and a combination of vapour induced phase separation (VIPS)-NIPS techniques varying the exposure time to humidity. This latter approach led to the formation of membranes with a porous architecture avoiding the use of any pore forming additive. The so-prepared membranes were, then, fully characterised in terms of morphology, polymorphism (in case of PVDF), wettability, thickness, porosity, pore size and water permeability. The membranes revealed different structures and a tuneable pore size in the range of ultrafiltration (UF) and microfiltration (MF) that render them ideal for applications in water treatment processes.

ACS Style

Francesca Russo; Francesco Galiano; Francesco Pedace; Fabio Aricò; Alberto Figoli. Dimethyl Isosorbide As a Green Solvent for Sustainable Ultrafiltration and Microfiltration Membrane Preparation. ACS Sustainable Chemistry & Engineering 2019, 8, 659 -668.

AMA Style

Francesca Russo, Francesco Galiano, Francesco Pedace, Fabio Aricò, Alberto Figoli. Dimethyl Isosorbide As a Green Solvent for Sustainable Ultrafiltration and Microfiltration Membrane Preparation. ACS Sustainable Chemistry & Engineering. 2019; 8 (1):659-668.

Chicago/Turabian Style

Francesca Russo; Francesco Galiano; Francesco Pedace; Fabio Aricò; Alberto Figoli. 2019. "Dimethyl Isosorbide As a Green Solvent for Sustainable Ultrafiltration and Microfiltration Membrane Preparation." ACS Sustainable Chemistry & Engineering 8, no. 1: 659-668.

Research article
Published: 28 May 2019 in ACS Sustainable Chemistry & Engineering
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A library of biofuel candidates 2,5-bis(alkoxymethyl) furans (BAMFs) was prepared from 2,5-bis(hydroxymethyl)furan (BHMF) by etherification in mild conditions using acid catalyst Purolite. The purification of the BAMFs has been assessed and gram scale experiments have been carried out for two specific examples. The efficiency of this synthetic approach to BAMFs was ascribed to the BHMF activated structure and its interaction with the aromatic acid catalyst.

ACS Style

Manuele Musolino; María José Ginés-Molina; Ramón Moreno-Tost; Fabio Aricò. Purolite-Catalyzed Etherification of 2,5-Bis(hydroxymethyl)furan: A Systematic Study. ACS Sustainable Chemistry & Engineering 2019, 7, 10221 -10226.

AMA Style

Manuele Musolino, María José Ginés-Molina, Ramón Moreno-Tost, Fabio Aricò. Purolite-Catalyzed Etherification of 2,5-Bis(hydroxymethyl)furan: A Systematic Study. ACS Sustainable Chemistry & Engineering. 2019; 7 (12):10221-10226.

Chicago/Turabian Style

Manuele Musolino; María José Ginés-Molina; Ramón Moreno-Tost; Fabio Aricò. 2019. "Purolite-Catalyzed Etherification of 2,5-Bis(hydroxymethyl)furan: A Systematic Study." ACS Sustainable Chemistry & Engineering 7, no. 12: 10221-10226.

Review
Published: 07 May 2019 in Frontiers in Chemistry
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This review focuses on the use of dialkyl carbonates (DACs) as green reagents and solvents for the synthesis of several 5- and 6-membered heterocycles including: tetrahydrofuran and furan systems, pyrrolidines, indolines, isoindolines, 1,4-dioxanes, piperidines, and cyclic carbamates. Depending on the heterocycle investigated, the synthetic approach used was different. Tetrahydrofuran systems, pyrrolidines, indolines, isoindoline, and 1,4-dioxanes were synthesized using dimethyl carbonate (DMC) as sacrificial molecule (BAc2/BAl2 mechanism). Cyclic carbamates, namely 1,3-oxazin-2-ones, were prepared employing DACs as carbonylating agents, either by BAc2/BAl2 mechanism or through a double BAc2 mechanism. Piperidines were synthetized taking advantage of the anchimeric effect of a new family of dialkyl carbonates, i.e., mustard carbonates. Finally, in the case 5-hydroxymethylfurfural (HMF), DMC has been employed as efficient extracting solvent of this extensively investigated bio-based platform chemical from the reaction mixture. These synthetic approaches demonstrate, once again, the great versatility of DACs and their-yet to be fully explored-potential as green reagents and solvents in the synthesis of heterocycles.

ACS Style

Pietro Tundo; Manuele Musolino; Fabio Aricò. Dialkyl Carbonates in the Green Synthesis of Heterocycles. Frontiers in Chemistry 2019, 7, 300 .

AMA Style

Pietro Tundo, Manuele Musolino, Fabio Aricò. Dialkyl Carbonates in the Green Synthesis of Heterocycles. Frontiers in Chemistry. 2019; 7 ():300.

Chicago/Turabian Style

Pietro Tundo; Manuele Musolino; Fabio Aricò. 2019. "Dialkyl Carbonates in the Green Synthesis of Heterocycles." Frontiers in Chemistry 7, no. : 300.

Feature
Published: 18 February 2019 in Synthesis
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A novel halogen-free synthesis of benzo-fused six-membered 1,4-heterocycles through the chemistry of dialkyl carbonates is reported. Commercially available catechol, 2-aminophenol, and 2-amino­thiophenol were reacted first with ethylene carbonate in an autoclave to give O-hydroxyethyl, N-hydroxyethyl, and S-hydroxyethyl derivatives respectively, through a BAl2 mechanism. Then 2-(2-hydroxyethoxy)phenol and 2-(2-hydroxyethylamino)phenol were cyclized in excellent yields by reaction with dimethyl carbonate (DMC) and DABCO as a bi­cyclic organic base to give the corresponding benzodioxine and benzoxazine derivative, respectively. Moreover, 2-(2-aminophenylthio)ethanol afforded the benzothiazine derivative in good yield by reaction with DMC with an excess of a strong base such as NaH. The investigation on the cyclization reaction has highlighted that several equilibria are involved leading to the formation of carbonate and carbamate intermediates through BAc2 mechanisms. Depending on the reaction conditions employed, these intermediates may undergo either kinetic-controlled ring closure by a BAl2 mechanism or by-product formation.

ACS Style

Manuele Musolino; Fabio Aricò. Benzo-Fused 1,4-Heterocycles via Dialkyl Carbonate Chemistry. Synthesis 2019, 51, 1770 -1778.

AMA Style

Manuele Musolino, Fabio Aricò. Benzo-Fused 1,4-Heterocycles via Dialkyl Carbonate Chemistry. Synthesis. 2019; 51 (08):1770-1778.

Chicago/Turabian Style

Manuele Musolino; Fabio Aricò. 2019. "Benzo-Fused 1,4-Heterocycles via Dialkyl Carbonate Chemistry." Synthesis 51, no. 08: 1770-1778.

Short communication
Published: 31 August 2018 in Journal of Cultural Heritage
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A sustainable methodology to synthesise and screen libraries of new low-environmental impact products, suitable for removing graffiti and murals from historic building, masonries and stone artworks has been developed. This approach provided a novel series of two-component systems by combining silica sol-gel chemistry and dimethyl carbonate. The solid matrixes were hybrid silica gels, which were synthesised in basic conditions by using ethylene and propylene glycols as organic co-solvents. Dimethyl carbonate (DMC) was the green organic solvent to load into the gel. The efficiency of three new systems in adsorbing/trapping commercial red aerosol spray paint was investigated through an ad hoc test tube extraction evaluation and on mock stained samples of Istrian stones. Data provided by NMR spectroscopy and FT-IR spectroscopy led to the identification of a promising cleaning agent, paving the way to its full characterisation and features improvement.

ACS Style

Manuele Musolino; Fabio Aricò; Pietro Tundo. An innovative and sustainable approach to spray paint graffiti removal from Istrian stone through the silica sol-gel chemistry: A preliminary assessment. Journal of Cultural Heritage 2018, 36, 268 -274.

AMA Style

Manuele Musolino, Fabio Aricò, Pietro Tundo. An innovative and sustainable approach to spray paint graffiti removal from Istrian stone through the silica sol-gel chemistry: A preliminary assessment. Journal of Cultural Heritage. 2018; 36 ():268-274.

Chicago/Turabian Style

Manuele Musolino; Fabio Aricò; Pietro Tundo. 2018. "An innovative and sustainable approach to spray paint graffiti removal from Istrian stone through the silica sol-gel chemistry: A preliminary assessment." Journal of Cultural Heritage 36, no. : 268-274.

Article
Published: 27 February 2018 in ChemistrySelect
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In this work, bio-based platform molecule 5-hydroxymethylfurfural (HMF) was synthesised under mild conditions (90 °C) from D-fructose using as media a mixture of dimethyl carbonate:tetraethyl ammonium bromide (DMC:TEAB). This solvent system resulted in a efficient production of HMF in the presence of both Amberlyst-15 (heterogeneous catalyst) and BF3O(Et)2 (homogeneous catalyst). HMF was recovered from the reaction mixture with or without minimal work-up. It is noteworthy that this synthetic approach provided high yielding product also when performed in a large-scale. Quick reduction of HMF to the related 2,5-bis(hydroxymethyl)furan was also conducted to further confirm the proposed procedure. Besides, the materials efficiency metrics of the optimized DMC-based synthetic approach have been compared to alternative syntheses for HMF reported in the literature. This latter study takes into consideration synthetic routes that employ D-fructose as substrate, easy accessible catalysts and report detailed procedures and evidence of the isolation of HMF.

ACS Style

Manuele Musolino; John Andraos; Fabio Aricò. An Easy Scalable Approach to HMF Employing DMC as Reaction Media: Reaction Optimization and Comparative Environmental Assessment. ChemistrySelect 2018, 3, 2359 -2365.

AMA Style

Manuele Musolino, John Andraos, Fabio Aricò. An Easy Scalable Approach to HMF Employing DMC as Reaction Media: Reaction Optimization and Comparative Environmental Assessment. ChemistrySelect. 2018; 3 (8):2359-2365.

Chicago/Turabian Style

Manuele Musolino; John Andraos; Fabio Aricò. 2018. "An Easy Scalable Approach to HMF Employing DMC as Reaction Media: Reaction Optimization and Comparative Environmental Assessment." ChemistrySelect 3, no. 8: 2359-2365.

Research article
Published: 12 December 2017 in The Journal of Organic Chemistry
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The reactivity of β-aminocarbonates as anisotropic electrophiles has been investigated with several phenols. Products distribution shows that the regioselectivity of the anchimerically driven alkylation reaction depends on the nucleophiles. The results suggest that in the presence of nucleophiles that are also good leaving groups, the reaction takes place under thermodynamic control favoring the attack on the most sterically hindered carbon of the cyclic aziridinium intermediate. Furthermore, when an enantiomerically pure pyrrolidine-based carbonate was used, the reaction with phenols proceeds via a bicyclic aziridinium intermediate leading to the stereoselective synthesis of optically active 3-substituted piperidines via ring expansion reaction. These results were confirmed both by NMR spectroscopy and X-ray diffraction analysis.

ACS Style

Fabio Aricò; Alexander S. Aldoshin; Manuele Musolino; Marco Crisma; Pietro Tundo. β-Aminocarbonates in Regioselective and Ring Expansion Reactions. The Journal of Organic Chemistry 2017, 83, 236 -243.

AMA Style

Fabio Aricò, Alexander S. Aldoshin, Manuele Musolino, Marco Crisma, Pietro Tundo. β-Aminocarbonates in Regioselective and Ring Expansion Reactions. The Journal of Organic Chemistry. 2017; 83 (1):236-243.

Chicago/Turabian Style

Fabio Aricò; Alexander S. Aldoshin; Manuele Musolino; Marco Crisma; Pietro Tundo. 2017. "β-Aminocarbonates in Regioselective and Ring Expansion Reactions." The Journal of Organic Chemistry 83, no. 1: 236-243.

Journals
Published: 30 October 2017 in Green Chemistry
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The worldwide urge to embrace a sustainable and bio-compatible chemistry has led industry and academia to develop chlorine-free methodologies focused on the use of CO2-based compounds, such as dimethyl carbonate, as feedstocks, promoters and reaction media.

ACS Style

P. Tundo; M. Musolino; F. Aricò. The reactions of dimethyl carbonate and its derivatives. Green Chemistry 2017, 20, 28 -85.

AMA Style

P. Tundo, M. Musolino, F. Aricò. The reactions of dimethyl carbonate and its derivatives. Green Chemistry. 2017; 20 (1):28-85.

Chicago/Turabian Style

P. Tundo; M. Musolino; F. Aricò. 2017. "The reactions of dimethyl carbonate and its derivatives." Green Chemistry 20, no. 1: 28-85.

Journal article
Published: 15 August 2017 in Pure and Applied Chemistry
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Cyclization of 2-(2-hydroxyethyl)phenol via DMC chemistry in acidic conditions is herein discussed for the first time. Reaction conditions have been investigated and optimized. This substrate is quite appealing as it incorporates a 2-hydroxyethyl moiety in ortho to the aromatic hydroxyl group capable of stabilizing the related phenonium ion. When the reaction mechanism was investigated via theoretical calculations, the results suggest that the most favorable pathway encompasses a DMC-mediated formation of the phenonium ion that is converted into the 2-(2-methoxyethyl)phenol. The related cyclic ether is then formed via intramolecular cyclization of this intermediate. This peculiar cyclization reaction is another example of the versatility of DMC herein used as solvent, methoxycarbonylation agent and leaving group in the intramolecular cyclization leading to the phenonium ion.

ACS Style

Fabio Aricò; Andrea Maranzana; Manuele Musolino; Pietro Tundo. 5-Membered cyclic ethers via phenonium ion mediated cyclization through carbonate chemistry. Pure and Applied Chemistry 2017, 90, 93 -107.

AMA Style

Fabio Aricò, Andrea Maranzana, Manuele Musolino, Pietro Tundo. 5-Membered cyclic ethers via phenonium ion mediated cyclization through carbonate chemistry. Pure and Applied Chemistry. 2017; 90 (1):93-107.

Chicago/Turabian Style

Fabio Aricò; Andrea Maranzana; Manuele Musolino; Pietro Tundo. 2017. "5-Membered cyclic ethers via phenonium ion mediated cyclization through carbonate chemistry." Pure and Applied Chemistry 90, no. 1: 93-107.

Article
Published: 22 December 2016 in ChemSusChem
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Direct synthesis of dimethyl isosorbide (DMI) from D-sorbitol via dimethyl carbonate (DMC) chemistry is herein firstly reported. High yield of DMI was achieved using nitrogen superbase 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as catalyst and performing the reaction in a stainless steel autoclave by increasing the temperature from 90°C to 200 °C. In this procedure DMC features its full capacity, acting in the different steps of the process as carboxymethylating, leaving group (cyclization) and methylating agent; DMC is also employed as the reaction media.

ACS Style

Fabio Arico'; A. S. Aldoshin; Pietro Tundo. One-Pot Preparation of Dimethyl Isosorbide fromd-Sorbitol via Dimethyl Carbonate Chemistry. ChemSusChem 2016, 10, 53 -57.

AMA Style

Fabio Arico', A. S. Aldoshin, Pietro Tundo. One-Pot Preparation of Dimethyl Isosorbide fromd-Sorbitol via Dimethyl Carbonate Chemistry. ChemSusChem. 2016; 10 (1):53-57.

Chicago/Turabian Style

Fabio Arico'; A. S. Aldoshin; Pietro Tundo. 2016. "One-Pot Preparation of Dimethyl Isosorbide fromd-Sorbitol via Dimethyl Carbonate Chemistry." ChemSusChem 10, no. 1: 53-57.