Article
Chemistry, Organic
Ke Yu, Qianjin Chen, Weiping Liu
Summary: An atom-economical and straightforward methodology for the synthesis of quinolines from alpha-2-aminoaryl alcohols and secondary alcohols is described. This protocol uses an Earth-abundant and air-stable iron catalyst under activating agent-free conditions, resulting in high yields and good functional group tolerance. Notably, the method allows for the synthesis of highly substituted fused polycyclic quinolines using secondary alpha-2-aminoaryl alcohols and beta-substituted secondary alcohols, achieving up to 94% isolated yields.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
C. Hernandez Mejia, D. M. A. Verbart, K. P. de Jong
Summary: The study investigated the use of hydrated niobium pentoxide and niobium phosphate in combination with a copper-based methanol synthesis catalyst for the direct synthesis of DME. While the three solid acids combined with the copper-based catalyst showed activity and selectivity in DME production, they all exhibited deactivation during the reaction.
Article
Chemistry, Multidisciplinary
Zhongxin Chen, Jingting Song, Xinwen Peng, Shibo Xi, Jia Liu, Wenhui Zhou, Runlai Li, Rile Ge, Cuibo Liu, Haisen Xu, Xiaoxu Zhao, Haohan Li, Xin Zhou, Lu Wang, Xing Li, Linxin Zhong, Alexandre I. Rykov, Junhu Wang, Ming Joo Koh, Kian Ping Loh
Summary: The study focuses on the development of mechanically strong, hierarchically porous carbon plates for the immobilization of single-atom catalysts (SACs) to enhance catalytic activity and stability. The carbon-based SACs exhibit excellent activity and selectivity for the synthesis of a wide assortment of quinolines through a three-component oxidative cyclization. The strategy is also applicable to challenging reactions such as the deuteration of quinolines at the fourth position.
ADVANCED MATERIALS
(2021)
Review
Chemistry, Multidisciplinary
Mohamad Reza Khodadadi, Julien Thiel, Rajender S. Varma, Christophe Len
Summary: Solketal is identified as a promising chemical for oleochemicals, particularly for ketalisation of glycerol. Recent advancements in catalytic ketalisation of glycerol in laboratories involve homogeneous, commercial heterogeneous, and specifically designed heterogeneous catalysts.
JOURNAL OF FLOW CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Suhong Song, Yuyu Dai, Yunyang Hong, Xiaoqing Li, Xinhuan Yan
Summary: This paper reports a new method for the continuous synthesis of 2-methylquinoline compounds using nitroarenes and the ethanol/water system through a simple hydrogen transfer reaction in the presence of the Ru-Fe/gamma-Al2O3 catalyst. The reaction is characterized by heterogeneity and continuity and uses green solvents, conforming to the principles of green chemistry. By studying the effects of different conditions on the yield of the product, it was found that this method can proceed smoothly and achieve high yield.
Article
Chemistry, Organic
Sunil Dutt, Vikas Tyagi
Summary: In this study, the synthesis of substituted quinolines via alpha-amylase catalyzed one-pot domino reactions was reported, showing high catalytic efficiency.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Nellya G. Grigorieva, Alsu Bayburtli, Olga S. Travkina, Sergey Bubennov, Rezeda Z. Kuvatova, Anna S. Artem'eva, Boris Kutepov
Summary: The activity, selectivity, and stability of microporous and hierarchical zeolites were studied in the synthesis of quinolines. It was found that hierarchical zeolites exhibited higher activity and selectivity, as well as better stability in the reaction compared to microporous zeolites.
Article
Chemistry, Organic
Kwihwan Kobayashi, Shingo Komatsuzaki, Shun-ya Onozawa, Koichiro Masuda, Shu Kobayashi
Summary: We present a green method for the synthesis of aryl enol ethers from phenols and dimethyl ketals using aluminium as a catalyst, without halides and transition metals. The ketal exchange reaction is driven by the removal of methanol. The obtained aryl enol ethers can be transformed into diaryl ethers through Pd/C-catalysed dehydrogenation or DDQ oxidation. This method is significant for the synthesis of important intermediates or building blocks in organic synthesis and polymer chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kwihwan Kobayashi, Shingo Komatsuzaki, Shun-ya Onozawa, Koichiro Masuda, Shu Kobayashi
Summary: We present an aluminium-catalysed, halide- and transition metal-free method for synthesizing aryl enol ethers from phenols and dimethyl ketals through ketal exchange driven by methanol removal. The obtained aryl enol ethers can be further transformed into diaryl ethers using Pd/C-catalysed dehydrogenation or DDQ oxidation. This new protocol provides a halide- and transition metal-free approach for the synthesis of phenols and dimethyl ketals, which are important intermediates or building blocks in organic synthesis and polymer chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Davide Rigo, Daniele Polidoro, Lorenzo Marcuzzo, Alvise Perosa, Maurizio Selva
Summary: Isopropenyl acetate (iPAc) can convert refined and crude glycerol (CG) into valuable products, such as allyl acetate, triacetin (TA), and acetal acetates, under continuous-flow conditions. This study presents two novel tandem catalytic protocols that achieve high yields of these products by using a combination of innocuous compounds with different roles. The importance of this research lies in providing a green and efficient method for the chemical upgrading of glycerol into valuable products, and improving the yields by optimizing process variables and catalyst selection.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Applied
Julian A. Vannucci, Nora N. Nichio, Francisco Pompeo
Summary: A series of acid catalysts were synthesized from a commercial zirconium oxide sulfated with a 0.5 M H2SO4 solution by wet impregnation. The sulfated zirconia calcined in air at 400 degrees C (Zr-S-400) showed the highest activity and stability for glycerol conversion, with a molar ratio S/Zr = 0.23. The estimated activation energy of the reaction based on a developed kinetic expression was 88.1 +/- 8.9 kJ/mol.
Article
Chemistry, Organic
Shuang-Shuang Sun, Zu-Yu Mo, Yan-Yan Chen, Yan-Li Xu
Summary: A simple and efficient method for the preparation of selenyl-substituted quinoline derivatives has been developed. This method allows for the rapid synthesis of 3-selenoacetyl quinoline and 3-diselenoacetyl quinoline derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Gabriel Abranches Dias Castro, Ana Luiza Quintao Santos, angel Gabriel Sathicq, Valeria Palermo, Gustavo Pablo Romanelli, Sergio Antonio Fernandes
Summary: This study proposed a method to convert glycerol into acetals using a sulfonic acid calix[4]arene catalyst supported on silica and microwave-assisted heating, and the quantitative analysis was performed using H-1 NMR. From the optimized conditions, twelve products with varying yields were obtained, and the reaction showed features such as solvent-free reaction, water as the sole waste, metal-free, and shorter reaction times.
REACTION CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Rajendran Satheeshkumar, Karnam Jayarampillai Rajendra Prasad, Wang Wen-Long, Christian Espinosa-Bustos, Cristian O. Salas
Summary: An interest in developing new 2-acetyl/propanoyl quinolines via Friedlander synthesis has been extensively studied. In this work, we successfully synthesized 2-acetylquinolines in high yields by using a freshly prepared Eaton's reagent as a catalyst without solvents. We also reported a novel regioselective solvent-free reaction for the synthesis of o-aminoarylketones with unsymmetrical 1,2-diketone, yielding different 2-propanoylquinolines. Eaton's reagent played a unique role in the reaction as a powerful desiccant, condensing agent, cyclizing agent, and dehydrating agent. It was found that Eaton's reagent is an inexpensive and easily accessible catalyst for the Friedlander synthesis.
Article
Chemistry, Physical
Hayette Alliouche, Houria Bouria, Rafik Bensegueni, Mounia Guergouri, Abdelmalek Bouraiou, Ali Belfaitah
Summary: In this paper, a combined experimental and theoretical study was conducted to synthesize and characterize new 2-quinolone-piperidine and -morpholine hybrids. The results from experiments were validated using computational calculations, and the affinity between these compounds and Acetylcholinesterase/Butyrylcholinesterase was estimated through molecular docking.
JOURNAL OF MOLECULAR STRUCTURE
(2024)
Article
Chemistry, Multidisciplinary
Daniele Polidoro, Alvise Perosa, Maurizio Selva
Summary: In this study, three different multiphase systems were investigated for the oxidation of 5-hydroxymethyl-furfural (HMF). The conditions for each system allowed for excellent control of the reaction selectivity and high yields of the desired products. The catalyst was efficiently segregated and recycled under all tested conditions.
Article
Chemistry, Physical
Nicola Bragato, Alvise Perosa, Maurizio Selva, Giulia Fiorani
Summary: A series of dihydroxybenzene-derived ILs were synthesized in a halide-free, eco-friendly manner and fully characterized. The most active catalyst for CO2 insertion into terminal epoxides to synthesize cyclic organic carbonates (COCs) was found to be methyltrioctylammonium hydroquinolate, [N-1888][HYD], under the proposed optimized conditions ([N-1888][HYD] 10% mol, T=120 degrees C, t=6 h, p(0)(CO2)=2.0 MPa, 12 examples, conversion >99%, yield up to 98%). Interestingly, [N-1888][HYD] also showed activity as a catalyst for CO2 insertion reactions with cyclohexene oxide (CHO), resulting in the formation of both COC and polycarbonate products. It is suggested that the catalytically active species for p(0)(CO2)>= 1.0 MPa is the hemicarbonate derivative of the hydroquinolate anion, which acts through an unusual hemicarbonate-alkoxide pathway for epoxide ring opening.
Article
Chemistry, Physical
Daniele Polidoro, Daily Rodriguez-Padron, Alvise Perosa, Rafael Luque, Maurizio Selva
Summary: Chitin, a renewable carbon and nitrogen source, is the second most abundant biopolymer on Earth after cellulose. This study successfully prepared chitin-derived N-doped carbonaceous materials functionalized with palladium metal nanoparticles. The physicochemical properties of these nanocomposites were investigated using a multi-technique approach, and their catalytic activity in reductive amination reactions was explored. Specifically, a biomass-derived platform molecule, furfural, was transformed into valuable bi-cyclic compounds under continuous flow conditions.
Article
Chemistry, Multidisciplinary
Daniele Polidoro, Irina Elena Mihai, Alvise Perosa, Maurizio Selva
Summary: Various multiphase systems consisting of immiscible liquid water, a hydrocarbon, and an ionic liquid were studied for the hydrogenation/hydrolysis of 5-hydroxymethylfurfural. A liquid triphase system composed of water, isooctane, and methyltrioctylammonium chloride achieved excellent selectivity control with high yields of the desired product. By separating the reagents and catalyst in different phases, the catalyst could be effectively recycled and reused multiple times without any loss of activity or selectivity.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Physical
Carlotta Campalani, Guillaume Petit, Jean-Christophe M. Monbaliu, Maurizio Selva, Alvise Perosa
Summary: Bass-CDs, synthesized from fishery waste, were used as a cheap and readily available photocatalyst in combination with oxygen and UV light for the efficient degradation of azo dyes. Both batch and continuous flow conditions were studied, and all the azo dyes were fully degraded, highlighting the suitability of bass-CDs for wastewater decontamination.
Review
Chemistry, Physical
Daniele Polidoro, Alvise Perosa, Maurizio Selva, Daily Rodriguez-Padron
Summary: Metal-free catalytic systems have become sustainable and cost-efficient heterogeneous catalysts, particularly in carbonaceous materials with various functionalities. This article provides an overview of recent advances in the design of such materials, focusing on biomass waste-derived materials and their structure-activity relationship. The potential applications of metal-free catalytic systems in different areas of catalysis and their use in upgrading renewable feedstocks are discussed. The article highlights the importance of sustainable approaches in terms of catalyst nature, non-toxic and sustainable precursors, synthetic protocol efficiency, and carbon footprint.
Article
Chemistry, Multidisciplinary
Daniele Polidoro, Maurizio Selva, Rafael Luque
Summary: An efficient continuous-flow (CF) protocol was developed for the hydrogenation of lignin-derived aromatics, producing high selectivity and conversion rates. The catalytic system exhibited excellent stability for over 420 minutes of continuous operation. A variety of substrates yielded ring-hydrogenated products with selectivity up to 99% at complete conversion.
Article
Chemistry, Multidisciplinary
Davide Rigo, Daniele Polidoro, Lorenzo Marcuzzo, Alvise Perosa, Maurizio Selva
Summary: Isopropenyl acetate (iPAc) can convert refined and crude glycerol (CG) into valuable products, such as allyl acetate, triacetin (TA), and acetal acetates, under continuous-flow conditions. This study presents two novel tandem catalytic protocols that achieve high yields of these products by using a combination of innocuous compounds with different roles. The importance of this research lies in providing a green and efficient method for the chemical upgrading of glycerol into valuable products, and improving the yields by optimizing process variables and catalyst selection.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Physical
Abdullah Hamadamin, Valentina Benazzi, Carlotta Campalani, Luca Quattri, Davide Ravelli, Faiq Hussain, Alvise Perosa, Maurizio Selva, Stefano Protti
Summary: Amorphous nitrogen-doped carbon dots (a-N-CDs) were synthesized via hydrothermal conditions using citric acid and diethylenetriamine (DETA) as carbon and nitrogen sources, respectively. These materials exhibit strong absorption in the visible light region and have been successfully used as photoredox catalysts under violet LED irradiation for the 1,2-difunctionalization of olefins through an atom transfer radical addition (ATRA) process. The reported approach offers a metal-free and aqueous medium synthesis route, highlighting the potential applications of these bio-derived carbon materials in organic synthesis.
Article
Chemistry, Multidisciplinary
Daniele Polidoro, Giancarmelo Stamilla, Matteo Feltracco, Andrea Gambaro, Alvise Perosa, Maurizio Selva
Summary: A single-step protocol for hydrolytic hydrogenation of microcrystalline cellulose into sorbitol was developed using commercial carbon-supported Ru as a catalyst, with gaseous CO2 as an acid source and molecular hydrogen as a reductant. By adjusting reaction parameters, such as temperature, time, and pressure, cellulose conversion of 81% was achieved at 220°C in 18 hours under 30 and 40 bar of H2 and CO2, respectively.
Article
Chemistry, Physical
Daniele Polidoro, Alina M. Balu, Maurizio Selva, Rafael Luque, Sameh M. Osman, Tripti Chhabra
Summary: Microwave (MW) and conventional heating (CH) methods were compared for the synthesis of fuel additives from levulinic acid. Phosphomolybdic acid (PMA) and phosphotungstic acid (PTA)-containing graphitic carbon nitride (GCN) were synthesized and optimized to achieve high yields. MW significantly reduced reaction times and is a more sustainable approach for the synthesis of various fuel additives. Scale-up experiments showed that MW with optimum GCN-PMA achieved higher productivity compared to CH conditions.
SUSTAINABLE ENERGY & FUELS
(2023)
Article
Chemistry, Multidisciplinary
Nicola Bragato, Alvise Perosa, Maurizio Selva, Giulia Fiorani, Roberto Calmanti
Summary: In this study, the syntheses, characterisation, properties comparison, and applications of molybdate and polyoxomolybdate ionic liquids as bifunctional catalysts for CO2 insertion into epoxides were described. The synthetic methods relied on anion exchange and acid-base reactions, including a novel route for the synthesis of molybdate ionic liquids using a halide-free organic precursor. The investigations showed that tetrabutylammonium molybdate could serve as an efficient catalyst for the production of hexane carbonate from 1,2-epoxyhexane under solventless and halide-free conditions.
Review
Chemistry, Multidisciplinary
Giulia Fiorani, Alvise Perosa, Maurizio Selva
Summary: This review provides a comprehensive analysis of the reactions and applications of various organic carbonates and enol esters for the functionalization and upgrading of renewable compounds. Five sections cover the synthetic methods of organic carbonates, their reactions as alkylating, carboxylating, and acylating agents, and their use as solvents. The review also discusses the pros and cons of different methods and suggests areas for future research and analysis.
Article
Chemistry, Physical
Daniele Polidoro, Daniel Ballesteros-Plata, Alvise Perosa, Enrique Rodriguez-Castellon, Daily Rodriguez-Padron, Maurizio Selva
Summary: A series of catalysts based on non-noble metal nanoparticles supported on chitin-derived N-doped carbons were prepared through a one-step protocol in the presence of EDTA as a ligand. The synthesized materials were tested in the catalytic oxidation of alcohols to aldehydes and ketones, and Mo-N/C materials exhibited the best performance.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Inorganic & Nuclear
Viviana Bressi, Thomas Len, Daniele Polidoro, Roberto Esposito, Michal Mazur, Maurizio Selva, Claudia Espro, Rafael Luque
Summary: This article discusses the preparation of straight lines of palladium particles on zinc oxide through wet impregnation, stabilizing the metal particles with the highly stepped morphology of ZnO that provides steric anchoring sites. The dispersed Pd/ZnO catalyst demonstrates significantly superior performance in the Suzuki-Miyaura cross-coupling reaction compared to Pd/Al2O3 and Pd/TiO2 catalysts.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.