Article
Chemistry, Multidisciplinary
Hiroki Tashiro, Masahiro Terada, Itaru Nakamura
Summary: Gold-catalyzed reactions were used to synthesize 2H-azirines with sulfenyl and acyl groups at the 3-position, yielding good to excellent results. These reactions involved internal transfer of sulfinyl oxygen atom and carbene insertion into the N-S bond for ring construction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
En-He Huang, Ying-Qi Zhang, Da-Qiu Cui, Xin-Qi Zhu, Xiao Li, Long-Wu Ye
Summary: A new copper-catalyzed Si-H bond insertion reaction involving N-propargyl ynamides and hydrosilanes has been discovered, providing an efficient method for the practical and atom-economic synthesis of valuable organosilanes in generally moderate to excellent yields under mild reaction conditions. This reaction also introduces a new pathway for Si-H bond insertion involving vinyl cations as key intermediates.
Article
Chemistry, Organic
Bijay Ketan Das, Tanumay Sarkar, Prabhat Kumar Maharana, Subhradeep Kar, Tharmalingam Punniyamurthy
Summary: In this study, stereospecific cascade C-N and C-O bonds formation of oxiranes with N-propargylamines was achieved using Zn/Ag relay catalysis, leading to the synthesis of functionalized dihydrooxazines. The reaction exhibited excellent tolerance towards various functional groups and was scalable for practical applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Inorganic & Nuclear
Pengcheng Gao, Michal Szostak
Summary: The catalytic addition of water to unsaturated C-C or C-N p bonds is an important and environmentally sustainable method for forming C-O bonds. Traditional acid-catalyzed hydration requires strong acids or toxic mercury salts, limiting its practical applications and posing safety and environmental concerns. Transition-metal-catalyzed hydration with NHC ligands has gained significant attention and has achieved major progress. This review provides a comprehensive overview of hydration reactions catalyzed by transition metal-NHC complexes and their applications in catalytic hydration.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Organic
Xiaodong Xiong, Jonathan Wong, Ying-Yeung Yeung
Summary: A facile, efficient, and chemoselective synthesis of allylic amides has been developed using allyl bromides activated by silver triflate. The Ritter-type reaction readily proceeds under mild conditions to give various allyl amides. This protocol is also applicable to different nucleophilic partners to yield a wide range of allyl-substituted products in the absence of a base.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Padinjare Veetil Saranya, Mohan Neetha, C. M. A. Afsina, Gopinathan Anilkumar
Summary: Multicomponent reactions (MCRs) can form highly functionalized compounds through the reaction between three or more reactants in a one-pot manner, providing products with the utilization of lesser resources and energy. MCRs adhere to the principles of green chemistry and have diverse applications across various fields.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yongquan Ning, Mengtian Huo, Lizuo Wu, Xihe Bi
Summary: A novel method for the stereoselective synthesis of alkynyl cyclopropanes, by the silver-catalyzed alkynylcyclopropanation of alkenes using alkynyl N-nosylhydrazones as alkynyl carbene precursors, is reported. This method provides a straightforward and powerful approach for preparing various alkynyl cyclopropanes in high yield with excellent stereoselectivities. In addition, the practicality of this method was demonstrated by gram-scale synthesis and late-stage modification of bioactive molecules.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Sajid Ur Rehman, Changkun Li
Summary: A highly regio- and enantioselective allylic sulfonation was achieved by using rhodium and bisoxazolinephosphine (NPN*) ligands, starting from racemic branched allylic carbonates and readily available sulfonylhydrazides under neutral conditions. The reaction produced branch-selective allylic sulfones with a >20:1 branch:linear ratio and >99% enantiomeric excess (ee) in <= 96% yield. Both Z and E linear allylic carbonates could also be transformed into the same chiral branched allylic sulfones with high regio- and enantioselectivities.
Article
Chemistry, Multidisciplinary
Chiara Costabile, Annaluisa Mariconda, Marco Sirignano, Alessandra Crispini, Francesca Scarpelli, Pasquale Longo
Summary: This study investigated the catalytic behavior of silver and gold complexes containing N-heterocyclic carbene ligands in A(3)-coupling reactions, revealing the higher efficiency of gold catalysts. Computational studies shed light on species possibly involved in the catalytic mechanism.
NEW JOURNAL OF CHEMISTRY
(2021)
Review
Chemistry, Physical
Jonathan Farhi, Ioannis N. Lykakis, George E. Kostakis
Summary: This study summarizes the multicomponent reaction of aldehydes, amines, and alkynes, known as A(3) coupling, and discusses the application and impact of metal-based catalytic systems in this transformation. By classifying substrates, synthetic methods, and various variables, a valuable database is created.
Review
Chemistry, Organic
Akash. G. G. Tathe, Sagar. S. S. Saswade, Nitin. T. T. Patil
Summary: Multicomponent reactions (MCRs) are an important branch in organic synthesis, allowing the construction of complex molecular structures from multiple starting materials in a single reaction. Traditionally, transition metals have been used as catalysts for MCRs, and numerous reviews have been published on this topic. Gold, on the other hand, offers unique reactivity profiles, enabling the synthesis of previously inaccessible molecules. In recent years, gold catalysts have emerged as powerful contenders for achieving MCRs with distinct mechanisms. This comprehensive review provides an overview of the state-of-the-art in the development of gold-catalyzed MCRs, with a focus on recent advancements.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Bo-Han Zhu, Cang-Hai Shen, Min-Ling Nie, Fumin Zheng, Chengzhe Huang, Fan Chen, Long Li, Chao Deng, Long-Wu Ye, Peng-Cheng Qian
Summary: In this study, a novel non-noble-metal-catalyzed oxidation/cyclization reaction has been developed to synthesize diversely functionalized lactams in moderate to good yields with excellent diastereoselectivities, without the production of typical cyclopropanation products. Furthermore, the combination with another chemical reaction allows for the high diastereo- and enantioselective synthesis of chiral gamma-lactams containing three contiguous stereocenters. Density functional theory calculations suggest that this reaction possibly involves a carbon cation or proton transfer process.
Article
Chemistry, Inorganic & Nuclear
Zexiong Pan, Jianying Zhang, Lulu Guo, Hao Yang, Jianfeng Li, Chunming Cui
Summary: The research synthesized cyclic (alkyl)(amino)carbene lanthanide complexes and characterized their structures through X-ray diffraction analysis, with density functional theory calculations demonstrating the predominantly ionic bond nature of the complexes. One of the complexes also demonstrated catalytic hydrosilylation of alkenes with high yields and Markovnikov selectivity.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mingbing Zhong, Xavier Pannecoucke, Philippe Jubault, Thomas Poisson
Summary: This paper describes the photocatalytic hydrosilylation of alkynes and alkenes under continuous flow conditions using a specific catalyst and blue LED light, resulting in good to excellent yields for a variety of alkenes and alkynes with high functional group tolerance. The reaction mechanism was studied, and a plausible scenario was proposed.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Puneet Singh Gahlaut, Deepak Gautam, Bhawana Shekhawat, Shivani Kushwaha, Barun Jana
Summary: Traditional methods for synthesizing large-scale propargylamines have limitations, while A3-coupling reactions have emerged as a potent alternative. In this study, we designed and synthesized two new inverse triazolyl-pyridine ligands and their Ag(i) complexes, which exhibited high catalytic activity in A3-coupling reactions.
NEW JOURNAL OF CHEMISTRY
(2023)
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
Chemistry, Physical
Ieva Goldberga, Nicholai D. Jensen, Christele Combes, Frederic Mentink-Vigier, Xiaoling Wang, Ivan Hung, Zhehong Gan, Julien Trebosc, Thomas-Xavier Metro, Christian Bonhomme, Christel Gervais, Danielle Laurencin
Summary: This study investigates the possibility of enriching O-17 isotopes in water molecules within hydrated biominerals using liquid assisted grinding. The results show that the labelled water molecules are mainly located at the core of the crystal structures and can enter the lattice through dissolution/recrystallization or diffusion. This work highlights the importance of high-resolution O-17 NMR in understanding the roles of water as a grinding agent and as a reagent for isotopic enrichment.
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, Physical
Gautier Felix, Nicolas Fabregue, Cesar Leroy, Thomas-Xavier Metro, Chia-Hsin Chen, Danielle Laurencin
Summary: The use of induction heating (i-BM) allows for heating the reaction media during ball-milling, expanding the nature and number of synthesized products. This method offers the advantages of fast heating, direct adaptability to commercially-available milling equipment, and the option to heat either the walls or the beads of the milling jars. The properties of the heating system can be finely tuned by manipulating the characteristics of the milling system and/or the induction heating conditions. Examples of applications include elucidating reaction mechanisms, synthesizing new molecules, and controlling the physical nature of milling media.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(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)
