Article
Chemistry, Applied
Marcos Lopes Araujo, Gilvan Aguiar Correia, Wagner Alves Carvalho, Lidia Sergeevna Shul'pina, Yuriy Nikitovich Kozlov, Georgiy Borisovich Shul'pin, Dalmo Mandelli
Summary: This paper investigated the oxidation of 2-butanol using different ligands in aqueous solutions. It was found that the addition of PCA, 5MPCA, and 3TFMPZOLE improved the reaction performance, while other ligands led to lower accumulation of products. DFT studies suggested that metal-ligand pi-back-bonding could be responsible for the reaction activity increase.
Review
Chemistry, Multidisciplinary
Alessandro Messori, Andrea Fasolini, Rita Mazzoni
Summary: This review discusses recent developments in homogeneous catalysts for the transformation of HMF, including the effects of metal nature, ligands, solvents, and reaction conditions. Current issues and future opportunities are also presented.
Article
Chemistry, Multidisciplinary
Callum R. Woof, Derek J. Durand, Natalie Fey, Emma Richards, Ruth L. Webster
Summary: The catalytic mechanism of iron-catalyzed alkene isomerization reaction was studied through a combination of experimental and theoretical approaches. The results suggest that the isomerization of alkenes can be achieved through the combination of a hydride source and an iron(II) beta-diketiminate pre-catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Shuxin Mao, Dennis Verspeek, Xiaodong Wen, Yong Yang, Yong-Wang Li, Kathrin Junge, Matthias Beller
Summary: A novel synthetic protocol for the direct oxidation of alkanes to give ketones and alcohols using hydrogen peroxide as oxidant under ambient conditions is presented. The catalyst for this transformation is conveniently generated by combining Fe salts with N-methyl bis(picolylamine) (Me-bpa). The addition of picolinic acid as an additive improves the yields of ketones and alcohols (32-57%). The reaction can be scaled up to multi-gram scale conveniently.
Article
Engineering, Environmental
Chenghao Zhang, Jing Luo, Binqi Xie, Wei Liu, Jisong Zhang
Summary: A continuous micro-packed bed reactor platform is developed to determine the kinetics of aerobic ethylbenzene oxidation in the presence of N-hydroxyphthalimide. The reactor system offers enhanced gas-liquid mass transfer, leading to a significant increase in the space-time yield of ethylbenzene oxidation compared to traditional batch reactors. Furthermore, the organic catalyst NHPI is covalently anchored on commercial activated carbon through an imidization reaction. The synthesized heterogeneous catalysts exhibit excellent performance in terms of acetophenone yield and turnover frequency (TOF).
CHEMICAL ENGINEERING JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Catriona C. James, Bas de Bruin, Joost N. H. Reek
Summary: The importance of transition metal catalysis lies in its wide range of applications, including the synthesis of chemicals, natural products, and pharmaceuticals. However, a relatively new application is the catalysis of new-to-nature reactions inside living cells. The complex environment of living cells poses challenges to transition metal catalysts due to the potential inhibition or deactivation by various biological components. In this review, we summarize the current progress in the field of transition metal catalysis, focusing on the evaluation of catalysis efficiency under living cell and biological conditions. Catalyst poisoning is a common issue in this field, and we suggest that future research should explore physical and kinetic protection strategies to enhance the reactivity of catalysts in cells.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Gabriela A. Correa, Susana L. H. Rebelo, Baltazar de Castro
Summary: Sustainable functionalization of renewable aromatics is crucial for the transition to a circular, fossil-free economy. In this study, typical stable aromatic compounds were successfully functionalized using a green catalytic system at room temperature. The results demonstrated unusual initial epoxidation of the aromatic ring, with high yields obtained for various products.
Article
Chemistry, Organic
Fanni Bede, Laszlo Kollar, Nandor Lambert, Peter Huszthy, Peter Pongracz
Summary: Palladium-catalyzed hydroaminocarbonylation reactions of olefins using aliphatic amines were successfully performed under carbon monoxide atmosphere. The targeted amides were synthesized in moderate to good isolated yields without the need for acidic additives. The effect of chiral diphosphines on product distribution, including chemo-, regio-, and enantioselectivities, was also investigated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Nadim Ayoub, Joumana Toufaily, Erwann Guenin, Gerald Enderlin
Summary: Lignocellulosic feedstocks can be used to generate biofuels and biochemicals, but methods using metal catalysts have some issues. This Review summarizes catalytic methods using metal and metal-free catalysts for oxidation reactions and demonstrates the potential of metal-free catalysts.
Article
Chemistry, Multidisciplinary
Dominik Neukum, Lorena Baumgarten, Dominik Wust, Bidyut Bikash Sarma, Erisa Saraci, Andrea Kruse, Jan-Dierk Grunwaldt
Summary: This study investigated the oxidation of unrefined HMF solutions obtained from saccharides in chicory roots, showing the critical role of base in increasing FDCA yield and the significant influence of amino acids from bio-sources on catalytic activity. A supported AuPd(2:1)/C alloy catalyst exhibited superior activity and stability.
Article
Biochemistry & Molecular Biology
Nuray Uzunlu, Peter Pongracz, Laszlo Kollar, Attila Takacs
Summary: In this research, bio-derived hemicellulose-based solvents, namely ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran, were used as green alternatives in palladium-catalyzed aminocarbonylation reactions. Optimization reactions were conducted using iodobenzene and morpholine under varying conditions, including temperature, pressure, and ligands. The study found that the XantPhos ligand significantly influenced the conversion (98%) and chemoselectivity (100% carboxamide) compared to the monodentate PPh3 ligand. Furthermore, the optimized conditions were applied to expand the range of substrates and amine nucleophiles.
Article
Chemistry, Multidisciplinary
Alexandra Walter, Wolfgang Eisenreich, Golo Storch
Summary: This study reports a photochemical approach using flavin catalysts to oxidize silyl enol ethers to α,β-unsaturated ketones. The catalysts exhibit good stability throughout the reaction and can be successfully applied in subsequent aerobic epoxidation reactions. The sequential catalytic activity of flavin enables rapid diversification of substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Marco Agnes, Arianna Mazza, Eszter Kalydi, Szabolcs Beni, Milo Malanga, Ilse Manet
Summary: By selectively irradiating Methylene Blue, a low-cost photocatalyst, four aromatic substrates were optimized to produce their corresponding endoperoxides in organic solvent. By combining hydrophobic substrates with a hydrophilic cyclodextrin (CyD) polymer, their photooxygenation in homogeneous aqueous environment was achieved. These results have potential applications in green homogeneous photocatalysis and delivery of oxygen releasing agents to tissues.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Alexandra M. Zima, Oleg Y. Lyakin, Anna A. Bryliakova, Dmitrii E. Babushkin, Konstantin P. Bryliakov, Evgenii P. Talsi
Summary: Catalytic approaches to late-stage creation of new C-O bonds, especially via oxygenation of particular C-H groups in complex organic molecules, provide challenging tools for the synthesis of biologically active compounds and candidate drugs. The key role of the oxygen-transferring high-valent iron-oxygen species in selective oxygenation is now well established. In this Personal Account, recent data on the reactivity of bioinspired formally oxoiron(V) catalytically active sites toward organic substrates having C=C and C(sp(3))-H groups are analyzed, with a focus on the factors governing the oxidation chemo- and stereoselectivity.
Article
Materials Science, Multidisciplinary
Titouan Montheil, Laurine Raimond, Laurine Valot, Marie Maumus, Matthieu Simon, Jean Martinez, Muriel Amblard, Daniele Noel, Ahmad Mehdi, Gilles Subra
Summary: We have developed a general methodology to synthesize and isolate hybrid silylated polysaccharides, which can be used to prepare cell-laden hydrogels through sol-gel polymerization in aqueous buffer and can be transformed into hybrid xerogels by freeze-drying. These materials have the potential to be used as biocompatible foams for biological applications.
ACS APPLIED POLYMER MATERIALS
(2022)
Article
Chemistry, Physical
Nicolas Petry, Florian Luttringer, Xavier Bantreil, Frederic Lamaty
Summary: Sydnones are important heterocyclic compounds with significant biological activities. This study reports the successful synthesis of diarylsydnones and iminosydnones using a mechanochemistry-based approach, which has potential applications in the development of new prodrugs and ligands of metal complexes. The ball-milling procedures proved to be efficient and time saving, while reducing the use of organic solvents.
FARADAY DISCUSSIONS
(2023)
Article
Biochemistry & Molecular Biology
Katarzyna Grychowska, Wojciech Pietrus, Ludmila Kulawik, Ophelie Bento, Grzegorz Satala, Xavier Bantreil, Frederic Lamaty, Andrzej J. Bojarski, Joanna Golebiowska, Agnieszka Nikiforuk, Philippe Marin, Severine Chaumont-Dubel, Rafal Kurczab, Pawel Zajdel
Summary: Salt bridge formation is a strong molecular non-covalent interaction in biological systems. This study investigated the influence of substitution pattern and geometry modifications on the quality of salt bridge formation in 5-HT6 receptor and D-3 receptor. The results showed that the modifications significantly improved the affinity and antagonist properties of the compounds at 5-HT6 receptor, but had no effect on D3 receptor. In silico experiments demonstrated that the applied modifications were beneficial for salt bridge formation at the 5-HT6 receptor, but unfavorable for D3 receptor.
Article
Biochemistry & Molecular Biology
Vittorio Canale, Wojciech Trybala, Severine Chaumont-Dubel, Paulina Koczurkiewicz-Adamczyk, Grzegorz Satala, Ophelie Bento, Klaudia Blicharz-Futera, Xavier Bantreil, Elzbieta Pekala, Andrzej J. Bojarski, Frederic Lamaty, Philippe Marin, Pawel Zajdel
Summary: In addition to the canonical Gs adenylyl cyclase pathway, the serotonin type 6 receptor (5-HT6R) recruits additional signaling pathways that control cognitive function, brain development, and synaptic plasticity in an agonist-dependent and independent manner. The development of biased ligands with different functional profiles at specific 5-HT6R-elicited signaling pathways may provide a novel therapeutic perspective in neurodegenerative and psychiatric diseases. A newly synthesized compound 3g exhibits neutral antagonist activity at the 5-HT6R-operated Gs signaling and inverse agonist activity at the Cdk5 pathway, making it a promising biased ligand to investigate the role of these signaling pathways in neurodegenerative diseases.
Article
Biochemistry & Molecular Biology
Nazarine Mokhtar, Marcin Drop, Florian Jacquot, Sylvain Lamoine, Eric Chapuy, Laetitia Prival, Youssef Aissouni, Vittorio Canale, Frederic Lamaty, Pawel Zajdel, Philippe Marin, Stephane Doly, Christine Courteix
Summary: Diabetic neuropathy can cause chronic pain and associated cognitive deficits. This study found that 5-HT6 receptor inverse agonists and rapamycin can alleviate mechanical hyperalgesia and cognitive deficits in a rat model of diabetic neuropathic pain. The 5-HT6 receptor ligands also showed efficacy in reducing tactile allodynia in other types of neuropathic pain. In addition, disrupting the interaction between 5-HT6 receptors and mTOR can alleviate both painful and cognitive symptoms in diabetic rats. Targeting the constitutive activity of 5-HT6 receptors or the 5-HT6 receptor-mTOR interaction could be valuable strategies for treating diabetic neuropathic pain and cognitive co-morbidities.
Article
Chemistry, Multidisciplinary
Charlene Lucas-Valmalle, Gilles Subra, Pascal Verdie, Marie-Lou Kemel, Valerie Dauge, Karine Puget, Jean Martinez
Summary: This study investigated the structure-activity relationships of acein by conducting displacement experiments using guinea pig brain membranes with high-affinity acein binding sites, using the labeled ligand [I-125]Tyr-Pro-Pro-Thr-Thr-Thr-Lys-Phe-Ala-Ala-OH. The results showed that the C-terminal pentapeptide H-Thr-Lys-Phe-Ala-Ala-OH is the minimal structure with high affinity for acein binding sites. Among the synthesized analogues, the pentapeptide H-Thr-Lys-Tyr-Ala-Ala-OH exhibited the highest binding affinity.
AUSTRALIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Katarzyna Grychowska, Uriel Lopez-Sanchez, Mathieu Vitalis, Geoffrey Canet, Grzegorz Satala, Agnieszka Olejarz-Maciej, Joanna Golebiowska, Rafal Kurczab, Wojciech Pietrus, Monika Kubacka, Christophe Moreau, Maria Walczak, Klaudia Blicharz-Futera, Xavier Bantreil, Gilles Subra, Andrzej J. Bojarski, Frederic Lamaty, Carine Becamel, Charleine Zussy, Severine Chaumont-Dubel, Piotr Popik, Hugues Nury, Philippe Marin, Laurent Givalois, Pawel Zajdel
Summary: The multifactorial origin and neurochemistry of Alzheimer's disease (AD) call for the development of multitarget treatment strategies. This study reports a first-in-class triple acting compound that targets serotonin type 6 and 3 receptors (5-HT-Rs) and monoamine oxidase type B (MAO-B) as an approach for treating AD.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Vittorio Canale, Michal Kaminski, Wojciech Trybala, Michal Abram, Krzysztof Marciniec, Xavier Bantreil, Frederic Lamaty, Jan Rodriguez Parkitna, Pawel Zajdel
Summary: A solid-state approach was used to synthesize compound PZ-1190, a multitarget ligand for serotonin and dopamine receptors with potential antipsychotic activity. The developed multistep mechanochemical protocol improved the overall yield, reduced the reaction time, and decreased the use of toxic reagents and organic solvents. The described procedures represent rare examples of mechanochemical reduction and aliphatic alcohol oxidation, which could be sustainable methods for obtaining crucial compounds.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Sebastien Lemouzy, Alienor Delavarde, Frederic Lamaty, Xavier Bantreil, Julien Pinaud, Sylvain Caillol
Summary: The synthesis of a new biobased aromatic diisocyanate from lignocellulosic raw material offers a greener approach for isocyanate production and the polyurethane industry. The conversion of bisguaiacol F into bisguaiacol F diamine was successfully achieved under mechanochemical and microwave conditions. The resulting diisocyanate was synthesized using a phosgene-free/room temperature protocol and showed potential as a biobased alternative to petrochemical-based diisocyanates.
Article
Chemistry, Multidisciplinary
Matthieu Lavayssiere, Frederic Lamaty
Summary: The solventless synthesis of an amide was successfully achieved using a twin-screw extruder with the aid of a coupling agent. This method proved to be highly productive and yielded satisfactory results for the preparation of APIs, specifically teriflunomide and moclobemide.
CHEMICAL COMMUNICATIONS
(2023)
Article
Polymer Science
Romain Tavernier, Lerys Granado, Monique Tillard, Louis Van Renterghem, Thomas-Xavier Metro, Frederic Lamaty, Leila Bonnaud, Jean-Marie Raquez, Ghislain David, Sylvain Caillol
Summary: A highly reactive 2-substituted benzoxazine monomer, Ph-fa[2]PhOH, was designed to lower the ROP temperature of commercial benzoxazine resins, resulting in significant improvement in resin properties.
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
