Article
Chemistry, Organic
Shuang-Shuo Niu, Yimin Liu, Yue Zhang, Xing-Chi Li, Jian Gong, Wanjian Ding, Ying Cheng
Summary: A simple and efficient two-step method was developed for the construction of novel 2,4,9a-trisubstituted-4a,9a-dihydroindeno-[2,1-d][1,3]oxazin-9-ones. The method exhibited good tolerance towards the substituents, substitution pattern, and steric hindrance of the o-alkenyl benzaldehydes. Furthermore, using this method, unprecedented dihydrobenzo[6,7]indeno[2,1-d][1,3]-oxazin-7-ones and dihydropyrido[2',3':3,4]cyclopenta[1,2-d][1,3]oxazin-9-ones were synthesized successfully.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hui Luo, Jing Ren, Ying Sun, Yunlin Liu, Feng Zhou, Guoyue Shi, Jian Zhou
Summary: Carbon dioxide (CO2) is a highly abundant and sustainable C1 building block for chemical synthesis, but its low reactivity and stability restrict its transformation into value-added chemicals. Recent advancements in flow chemistry have enabled effective and continuous transformations of CO2, utilizing the advantages of continuous flow platforms. This article provides an update on the latest developments in this research area, highlighting the need for continuous CO2 transformation.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Anastasiya Agafonova, Pavel A. Sakharov, Ilia A. Smetanin, Nikolai Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: A fundamentally new radical cascade reaction of 2-acyloxyazirines provides a one-step method for the preparation of 5-hydroxy-6H-1,3-oxazin-6-ones. The reaction can be applied to various 2-acyloxy-substituted methyl azirine-2-carboxylates, with the volume of the acyloxy substituent influencing the formation of a side product. Additionally, the hydroxyl group in the resulting product can be easily replaced with different groups through palladium-catalyzed cross-coupling reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Xuetong Li, Jordi Benet-Buchholz, Eduardo C. Escudero-Adan, Arjan W. Kleij
Summary: A conceptually novel catalytic domino approach is presented for the synthesis of highly functional 1,4-dihydro-2H-1,3-benzoxazine-2-one derivatives. The chemoselectivity is achieved through a proper design of the precursor and the use of Thorpe-Ingold effects. The synthetic diversity of these CO2-based heterocycles is demonstrated, and an unusual ring-expansion sequence is observed from an alpha-alkylidene, five-membered cyclic carbonate to a six-membered cyclic carbamate by N-induced isomerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jaume Rostoll-Berenguer, Murta Capella-Argente, Gonzalo Blay, Jose R. Pedro, Carlos Vila
Summary: This study presents a direct sp(3) C-H amination of cyclic amines (dihydroquinoxalinones and dihydrobenzoxazinones) accelerated by visible-light irradiation under metal and photocatalyst-free conditions. The protocol offers mild reaction conditions and high yields for the synthesis of aminal quinoxaline and benzoxazine derivatives, serving as versatile building blocks for the divergent synthesis of quinoxalin-2-one derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sandeep Kumar, Prince, Mohit Gupta, Ram Sunil Kumar Lalji, Brajendra K. Singh
Summary: A microwave-assisted, palladium-catalyzed regioselective halogenation of 3-phenyl-2H-benzo[b][1,4]oxazin-2-ones has been successfully demonstrated using N-halosuccinimide. The reaction proceeds with good to moderate yields, utilizing the nitrogen atom of the heterocyclic ring as a directing group. This cost-effective and time-saving method shows wide substrate scope, high functional group tolerance, and high atom and step economy, providing potential for post-functionalization.
Article
Chemistry, Multidisciplinary
Hiroki Koizumi, Katsuhiko Takeuchi, Kazuhiro Matsumoto, Norihisa Fukaya, Kazuhiko Sato, Masahito Uchida, Seiji Matsumoto, Satoshi Hamura, Jun-Chul Choi
Summary: The authors propose an efficient method for synthesizing urea derivatives from low concentrations of CO2 present in the environment, without the need for complex separation and concentration processes. This one-pot approach directly converts CO2 from exhaust gases into industrially important chemicals.
COMMUNICATIONS CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Titu Mondal, Jhumur Seth, Somnath Sarkar, Sk Manirul Islam
Summary: Recently, the conversion of carbon dioxide into important fine chemicals has gained attention due to its abundance as a C1 source. A single-step synthesis of a SO3H-anchored covalent organic framework (COF) has been introduced in this study. The COF showed a large surface area and acted as a catalyst for the carbamate synthesis reaction from epoxides and amines in the presence of CO2. It exhibited excellent catalytic activity with high yield and could be easily separated and reused.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Showkat Ahmad Bhat, Mohammad Yaqoob Bhat, Suhail Ahmad Rather, Salman Jameel, Khursheed Ahmad Bhat, Qazi Naveed Ahmed
Summary: An unprecedented one-step strategy for synthesizing 5-(methylthio)pyridazin-3(2H)-one derivatives has been developed through iodine triggered deaminative coupling. This strategy involves the reaction of glycine esters with methyl ketones and hydrazine hydrate in DMSO. The transformations, in the absence of hydrazine, generated various 3-methylthio-4-oxo-enoates in good yields. Notably, DMSO played multiple roles as an oxidant, methylthiolating reagent, and solvent.
Article
Energy & Fuels
Yidan Ouyang, Bin Lei, Zhouqing Tan, Fen Hu, Zhao Wu, Jiaxue Wang, Yixuan Ma, Ran Zhang, Li Guo, Feifei Chen
Summary: Lignin waste can be upgraded into a catalyst with outstanding catalytic activity for transforming CO2 into high-value chemicals through the acid gradient grading method. The enriched COOH and Ar-OH groups in lignin contribute to the enhanced catalytic performance.
Article
Engineering, Environmental
Mehar Singh, Abhinav Kapur, Moondeep Chauhan, Gurpreet Kaur, Ajeet Kaushik, Ganga Ram Chaudhary
Summary: Novel and green arginine-capped hafnium oxide nanoparticles (L-Arg@HfO2 NPs) were developed for selective electrochemical sensing of mercuric ions (Hg2+). The L-Arg@HfO2 NPs exhibited spherical morphology and biocompatibility, providing selectivity for Hg2+ sensing. The sensor responded linearly to Hg2+ ions in the concentration ranging from 2 to 140 μM with a low detection limit of 152.58 nM, and showed reproducibility, stability, reusability, and selectivity towards Hg2+ in real water samples.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
ShiJun Chen, Jianshan Li, Li'an Yang, Jinzhu Chen, Rahele Zhiani
Summary: Biogenic dendritic fibrous Dy2Sn2O7 (Dy2Sn2O7 BDF) were greenly synthesized with the presence of Desulfovibrio alaskensis G20 using tin(IV) chloride pentahydrate and Dy(NO3)3.5 H2O as sources of tin and dysprosium. Various approaches were employed to investigate the specimens created with Desulfovibrio alaskensis G20. The properties of Dy2Sn2O7 BDF as a nanocatalyst were determined through EDS, TGA, TEM, XRD, and SEM, revealing its high ionic internal character, mechanical and thermal sustainability, and persistent colloidal stability.
JOURNAL OF CO2 UTILIZATION
(2023)
Article
Chemistry, Physical
Swapna M. Gade, Vitthal B. Saptal, Bhalchandra M. Bhanage
Summary: This review discusses the synthesis, properties, and applications of glycerol carbonate (GC). The conversion of glycerol (GLY) to GC via transesterification is considered the most promising route. The effects of catalysts and operating conditions on GC yield are summarized, and future directions for GC production are discussed.
CATALYSIS COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Leonardo de Oliveira Sartori, Amauri Alves Souza, Felipe Sanchez Bragagnolo, Gabriel Cassia Fortuna, Filipe Pereira Giardini Bonfim, Valeria Cristina Rodrigues Sarnighausen, Renato Lajarim Carneiro, Cristiano Soleo Funari
Summary: A new UHPLC-UV protocol was developed for more efficient and environmentally friendly determination of bitter acids and xanthohumol in hops and their derivatives. The method allows for enhanced sample throughput and potentially increases the safety of the analyst by providing baseline separations for the major bitter acids and xanthohumol.
Article
Chemistry, Organic
Qi Cui, Tony W. Pan, Meg Shieh, Shane S. Kelly, Shi Xu, Wei-Jun Qian, Ming Xian
Summary: In this study, we predicted the reactivity of strained alkynes with sulfur-containing analogues through computational studies. Experimental results confirmed the predictions, showing that 2H-pyan-2-thiones were the most reactive substrates. This reaction was effective in aqueous buffers and cellular environments, producing COS as a byproduct which could be converted into H2S.
Article
Chemistry, Multidisciplinary
Giulia Marafon, Marco Crisma, Anna Masato, Nicoletta Plotegher, Luigi Bubacco, Alessandro Moretto
Summary: Proteins undergo changes in their 3D structure and function through specific molecular interactions, which is crucial for sensing, processing, and transmitting information from the surrounding environment. The study of early aggregation steps of alpha-synuclein associated with Parkinson's disease showed that light-mediated binding with a photoactive foldamer can promote the process by generating supramolecular fibrillar seeds that act as molecular templates for inducing fast beta-sheet transitions in monomers. This proposed method provides a powerful tool for studying protein aggregation in misfolding diseases in a controlled and inducible system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Fabio Arico
Summary: This article provides a comprehensive overview of the synthetic procedures for 2,5-bis(hydroxymethyl)furan (BHMF), a stable bio-based diol with various applications. The advantages, limitations, and potential future developments of different synthetic approaches for BHMF are discussed to explore its potential in the biorefinery market.
PURE AND APPLIED CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Angel Gabriel Sathicq, Mattia Annatelli, Iskandar Abdullah, Gustavo Romanelli, Fabio Arico
Summary: Several alkyl carbonate derivatives of HMF and BHMF have been synthesized for the first time with high yields and pure compounds recovered under mild reaction conditions. These new products are stable over time and suitable as monomers for new bio-based polycarbonates and polyurethanes.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2021)
Article
Chemistry, Multidisciplinary
Giacomo Trapasso, Mattia Annatelli, Davide Dalla Torre, Fabio Arico
Summary: A convenient and simple one-pot method for the synthesis of 2,5-furandicarboxylic acid dimethyl ester (FDME) from galactaric acid using dimethyl carbonate (DMC) chemistry is presented in this study. The optimal reaction conditions were determined to be the reaction of galactaric acid with DMC in the presence of Amberlyst-36 at 200 degrees C for 2 hours. Under these conditions, FDME was obtained as the main product with a 70% yield. The reaction intermediates were identified and a possible reaction mechanism was proposed.
Article
Chemistry, Organic
Monica Viviano, Giacomo Trapasso, Mattia Annatelli, Ciro Milite, Sabrina Castellano, Fabio Arico
Summary: A microwave-assisted chlorine-free direct phenol substitution method was developed, which is considered as a significant research area in green chemistry for pharmaceutical manufacturers. The reaction of beta-aminocarbonates with substituted phenols using a polar solvent resulted in the formation of aminoalkylated products. The microwave irradiation also promoted the one-pot aminoalkylation of phenol in excellent yield.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Giacomo Trapasso, Claudio Salaris, Marco Reich, Evgenia Logunova, Cristiano Salata, Klaus Kuemmerer, Alberto Figoli, Fabio Arico
Summary: In this work, a scale-up procedure for the production of non-commercial or expensive dialkyl carbonates (DACs) was explored. The procedure involved a transcarbonylation reaction of an alcohol with dimethyl carbonate, catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). The customized procedure allowed for large-scale production of DACs and addressed issues such as purification and recycling of excess reagents. The properties and environmental impact of the new DACs were evaluated through software modeling and experimental tests.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2022)
Article
Chemistry, Multidisciplinary
P. L. Aldred, F. Leroux, H. M. Colquhoun, F. Arico
Summary: The highly-oriented fibres of aromatic polyetherketone obtained through nucleophilic polycondensation have been studied using X-ray diffraction. The diffraction data show that the existing models for the crystal and molecular structure of this polymer are not compatible with the experimental results. A novel structure based on a six-ring crystallographic repeat has been proposed, which matches well with the experimental pattern.
MATERIALS TODAY CHEMISTRY
(2022)
Article
Chemistry, Applied
Fabio Arico, Giacomo Trapasso, Giovanna Mazzi, Beatriz Chicharo, Mattia Annatelli, Davide Dalla Torre
Summary: In this study, a multigram-scale procedure for the synthesis of 5-hydroxymethylfurfural (HMF) was developed. By reacting D-fructose with Purolite CT275DR and utilizing a dimethyl carbonate/tetraethyl ammonium bromide system, HMF can be synthesized efficiently on an industrial scale.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Green & Sustainable Science & Technology
Mattia Annatelli, Giacomo Trapasso, Davide Dalla Torre, Luca Pietrobon, Davide Redolfi-Bristol, Fabio Arico
Summary: In this study, a green synthetic approach to 5,5'-(oxybis(methylene)]bis-2-furfural (OBMF) from 5-hydroxymethyl-2-furfural (HMF) is reported. The reaction conditions were optimized, using dimethyl carbonate (DMC) as the solvent and iron(III) sulfate as the catalyst. OBMF and its derivatives showed high yields and thermal stability, making them valuable bio-based monomers for bioplastics preparation.
ADVANCED SUSTAINABLE SYSTEMS
(2022)
Article
Chemistry, Multidisciplinary
Giacomo Trapasso, Francesca Russo, Francesco Galiano, Con Rob McElroy, James Sherwood, Alberto Figoli, Fabio Arico
Summary: Membrane processes are widely used in various industrial applications such as separation of mixtures, hydrogen isolation, CO2 removal, and wastewater treatment. In this study, organic carbonates were used as green media for membrane preparation. Theoretical thermodynamic studies were conducted to predict the solubilities of different polymers commonly used for membrane preparation in dialkyl carbonates (DACs). Results showed that membranes prepared with custom-made DACs exhibited better structural resistances and smaller pore sizes compared to those using commercially available cyclic organic carbonates. These findings highlight the versatility of DACs as green solvents.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Polymer Science
Amandine L. Flourat, Mattia Annatelli, Sami Fadlallah, Fabio Arico, Florent Allais
Summary: A new class of furanic alpha,omega-dienes was synthesized using cellulose-derived starting material, and their properties in acyclic diene metathesis polymerization were investigated. The resulting biobased polyethers showed high molecular weights and good thermal stability, with low glass transition temperatures. The use of green solvents and copolymerization experiments were explored to improve the performance of the polyethers.
Article
Chemistry, Physical
Giacomo Trapasso, Beatriz Chicharo, Thomas Gherardi, Davide Redolfi-Bristol, Fabio Arico
Summary: In this study, an alternative green synthetic approach to FDCA methyl ester (FDME) using galactaric acid as the substrate, dimethyl carbonate (DMC) as the green media, and Fe-2(SO4)(3) as the heterogeneous Lewis acid was reported. Optimization of the reaction conditions allowed for a 70% isolated yield of FDME. Product purification was achieved through flash column chromatography over silica. Furthermore, it was possible to employ up to 5.0 g of galactaric acid in a single reaction, leading to a good isolated yield of FDME.
Article
Humanities, Multidisciplinary
Rosa Costantini, Eleonora Balliana, Davide Dalla Torre, Fabio Arico, Elisabetta Zendri
Summary: This study investigated the effects of ethanol and isopropanol solutions on silk artifacts and found that there were no significant chemical and physical changes on silk fibers even after immersion for 180 minutes. However, solutions containing BZK significantly increased the water wettability of silk.
Article
Chemistry, Multidisciplinary
Sami Fadlallah, Aihemaiti Kayishaer, Mattia Annatelli, Louis M. M. Mouterde, Aurelien A. M. Peru, Fabio Arico, Florent Allais
Summary: Cellulose-derived photocrosslinkable polycarbonates with renewable citronellol pendant chains were synthesized and four repeating units were identified in the polymer structure. The relative percentages of the repeating units and molecular weights of the polymers can be finely tuned by varying the catalyst and reaction conditions. The synthesized polymers exhibited low glass transition temperatures and high thermal decomposition temperatures. The citronellol pendant chains could be crosslinked via ultraviolet irradiation to further control the polymer properties.
Article
Chemistry, Physical
Mattia Annatelli, Davide Dalla Torre, Manuele Musolino, Fabio Arico
Summary: In this study, a comprehensive investigation was conducted on the high-yielding methylation of isosorbide via DMC chemistry promoted by the nitrogen organocatalyst N-methyl pyrrolidine (NMPy). The optimized reaction conditions were efficiently applied for the methylation of isosorbide epimers, isoidide, and isomannide, as well as for some preliminary scale-up tests. The role of NMPy in the methylation of isosorbide was elucidated through the synthesis, isolation, and characterization of all seven methyl and methoxycarbonyl intermediates observed in the etherification process.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
