Review
Acoustics
Ingrid V. Machado, Jhonathan R. N. dos Santos, Marcelo A. P. Januario, Arlene G. Correa
Summary: By utilizing ultrasound-assisted multicomponent reactions under heterogeneous catalysis, it is possible to efficiently synthesize biologically active organic compounds with reduced costs and energy consumption.
ULTRASONICS SONOCHEMISTRY
(2021)
Article
Chemistry, Organic
Xianjun Xu, Huangdi Feng, Erik V. Van der Eycken
Summary: An efficient synthesis route for unsymmetric 1,4-diamino-2-butynes has been developed using a microwave-assisted Cu(I)-catalyzed cross-A(3)-coupling/decarboxylative coupling process. The multicomponent reaction yields target products in moderate to good yields with high chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ahmad Reza Moosavi-Zare, Mohammad Rezaei-Gohar, Mahsa Tavasoli, Hamid Goudarziafshar
Summary: N-Sulfopyridin-1-ium monozinc(II) trichloride ([NSPy]ZnCl3) was prepared and used as a multipurpose catalyst for the synthesis of propargylamines by the A(3) coupling reaction of aromatic aldehydes, alkynes, and secondary amines under mild conditions. The carbonyl group in the aldehyde was activated by the acidic part in the catalyst, while zinc was responsible for the C-H activation of phenylacetylene.
Letter
Chemistry, Organic
Showkat Ahmad Bhat, Mohammad Yaqoob Bhat, Suhail Ahmad Rather, Salman Jameel, Khursheed Ahmad Bhat, Qazi Naveed Ahmed
Summary: An unprecedented one-step synthesis of 5-(methylthio)pyridazin-3(2H)-one derivatives has been achieved through iodine triggered deaminative coupling of glycine esters, methyl ketones, and hydrazine hydrate in DMSO. The absence of hydrazine allowed the generation of various 3-methylthio-4-oxo-enoates in good yields. DMSO played multiple roles as an oxidant, methylthiolating reagent, and solvent.
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.
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
Chemistry, Physical
Raed H. Althomali, Mohammed Khalid Abbood, Farag M. A. Altalbawy, Ebraheem Abdu Musad Saleh, Sherzod Shukhratovich Abdullaev, Ahmed Jaber Ibrahim, Shakeel Ahmed Ansari, Rosario Mireya Romero-Parra
Summary: A novel nanomagnetic NHC-Palladium complex was successfully prepared through post-synthetic modification (PSM) condensation and chelation of Pd ions. The [Fe3O4@bisimidazolium-Pd]2Cl- complex showed excellent catalytic performance in synthesizing propargylamines. It can be reused seven times without any loss of its catalytic ability, indicating its stability in reactions.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Hyun Jo Kim, Ji Eun Lee, Ganesh Koyyada, Mohan Lakavathu, Jae Hong Kim
Summary: In this study, a straightforward approach using 1,10-phenanthroline copper(I) complexes as a catalyst for the coupling reaction between alkynes and amines was reported. This method can be used to generate polyfunctional amino analogues. The addition of zinc halide or the use of Sc(OTf)(3) allowed the transformation of the products into different compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Polymer Science
Guoqiang Liu, Ruihao Pan, Yen Wei, Lei Tao
Summary: The Hantzsch reaction is a powerful tool for synthesizing 1,4-dihydropyridine derivatives, and has recently been introduced into polymer chemistry for developing polymers with new functions. These polymers with 1,4-DHP structures have potential applications in various fields. The future development of the Hantzsch reaction is promising for exploring new functional polymers.
MACROMOLECULAR RAPID COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Ryou Kubota, Itaru Hamachi
Summary: Living cells are capable of integrating multiple bio-supramolecules to carry out complex physiological functions. Synthetic supramolecular systems that mimic cell-like responses and functions are desired. Recent progress in constructing multicomponent supramolecular soft materials through hybridization of supramolecules with functional molecules is highlighted. These materials exhibit bioinspired responses to stimuli and offer promise for applications in soft robotics, disease diagnosis, and tissue regeneration.
Review
Chemistry, Multidisciplinary
Yasmin Wahby, Hamida Abdel-Hamid, Mohammed Salah Ayoup
Summary: Passerini three-component reactions based on isonitriles are impressive synthetic protocols that provide poly-functionalized compounds in a one-pot process. Recent advances in Passerini reactions have shown potential applications in the pharmaceutical field and the synthesis of various compounds over the past two decades.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Physical
Dominik Birnthaler, Rok Narobe, Eliseo Lopez-Berguno, Christoph Haag, Burkhard Koenig
Summary: Ligand-to-metal charge transfer (LMCT) photo-catalysis enables the activation and utilization of halides and other heteroatoms in metal complexes. The application of bismuth LMCT in organic radical coupling reactions has been expanded, generating chlorine and carboxyl radicals in net-oxidative and redox-neutral photochemical reactions. The study reveals BiCl4- and BiCl52- as the catalytically active bismuth species under 385 nm irradiation, providing insight into the reactivity of the highly reactive bismuth(II) catalyst fragment through cyclic voltammetry and UV-vis studies.
Review
Chemistry, Inorganic & Nuclear
Leandros P. Zorba, Georgios C. Vougioukalakis
Summary: Green chemistry and sustainable catalysis are gaining more attention, with multicomponent reactions such as the A(3) coupling offering a superior, more efficient approach compared to traditional methods.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Organic
Huangdi Feng, Futao Peng, Hui Xi, Ling Zhong, Liliang Huang
Summary: The study presents a simple method for synthesizing propargylamines, with high yields achieved by controlling the loading of amines to increase selectivity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Joana F. Campos, Veronique Ferreira, Sabine Berteina-Raboin
Summary: The study demonstrates the use of eucalyptol as a bio-based solvent for various reactions on heterocycles, highlighting its potential as a sustainable alternative in therapeutically active compounds.
Review
Chemistry, Multidisciplinary
Xiao Tang, Songtao Ding, Liangliang Song, Erik V. V. Van der Eycken
Summary: The isoindolo[2,1-b]isoquinolin-5(7H)-one scaffold is a widely found core structure in many bioactive natural products. Transition metal-catalyzed C-H activation/annulation has emerged as a powerful method to construct diverse polyheterocycles and has been employed for the synthesis of isoindolo[2,1-b]isoquinolin-5(7H)-one. This review provides an overview of recent advances in the preparation of isoindolo[2,1-b]isoquinolin-5(7H)-ones using transition metal-catalyzed C-H activation/annulation, aiming to help researchers discover hidden opportunities and accelerate the discovery of novel transformations based on C-H activation/annulation.
Article
Chemistry, Organic
Javier E. Alfonso-Ramos, Ruben Van Lommel, David Hernandez-Castillo, Frank De Proft, Roy Gonzalez-Aleman, Erik V. Van der Eycken, Gerardo M. Ojeda-Carralero
Summary: 3-Dipolar cycloadditions are commonly used to form five-membered heterocycles, but the cycloadditions involving acyl-isocyanide ylides have not been well explored by the chemical community. In this study, we investigated the mechanistic features of the reaction between acyl-isocyanide ylides and dipolarophiles using density functional theory calculations. We explained the experimental results and predicted opposite regioselectivity for electron-poor and electron-rich dipolarophiles. This study provides insights for the design of new cycloaddition reactions based on the acyl-isocyanide ylides motif.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Health Care Sciences & Services
Christiaan Vis, Josien Schuurmans, Bruno Aouizerate, Mette Atipei Craggs, Philip Batterham, Leah Buhrmann, Alison Calear, Arlinda Cerga Pashoja, Helen Christensen, Els Dozeman, Claus Duedal Pedersen, David Daniel Ebert, Anne Etzelmueller, Naim Fanaj, Tracy L. Finch, Denise Hanssen, Ulrich Hegerl, Adriaan Hoogendoorn, Kim Mathiasen, Carl May, Andia Meksi, Sevim Mustafa, Bridianne O'Dea, Caroline Oehler, Jordi Piera-Jimenez, Sebastian Potthoff, Gentiana Qirjako, Tim Rapley, Judith Rosmalen, Ylenia Sacco, Ludovic Samalin, Mette Maria Skjoth, Kristine Tarp, Ingrid Titzler, Erik Van der Eycken, Claire Rosalie van Genugten, Alexis Whitton, Enrico Zanalda, Jan H. Smit, Heleen Riper
Summary: This study compared the effectiveness of the ItFits-toolkit with implementation-as-usual in implementing iCBT services in routine mental health care organizations. The ItFits-toolkit performed better in supporting implementers in developing and applying effective tailored implementation strategies, but had a small effect on normalization levels among service providers.
JOURNAL OF MEDICAL INTERNET RESEARCH
(2023)
Review
Chemistry, Multidisciplinary
Xiao Tang, Liangliang Song, Erik V. Van Der Eycken
Summary: The Ugi reaction is highly explored due to its mild reaction conditions, wide scope, and high variability for the formation of multifunctional adducts. By carefully selecting the starting four components, Ugi-adducts can undergo different post-transformations to synthesize bioactive heterocycles, natural products, and macrocycles. Various post-Ugi transformations have been developed for constructing structurally novel polycycles, and this account summarizes important efforts for the synthesis of polycyclic N-heterocycles via post-Ugi cyclizations from the Van der Eycken laboratory onwards 2016. With the aid of transition metal catalysis and metal-free strategies, versatile polyheterocycles are prepared with high efficiency and step-economy.
Review
Chemistry, Multidisciplinary
Xianjun Xu, Ling Zhong, Huangdi Feng, Erik V. V. Van Der Eycken
Summary: The metal-free dearomatization reactions have proven to be a green and sustainable method for constructing spirocyclic, polycyclic, and heterocyclic scaffolds. This review focuses on recent advances in metal-free dearomatization reactions, including organo-catalyzed, oxidative, Bronsted acid- or base-promoted, photoredox-catalyzed, and electrochemical oxidation dearomatization reactions.
Article
Chemistry, Multidisciplinary
Laura Y. Vazquez-Amaya, Guglielmo A. Coppola, Erik V. Van der Eycken, Upendra K. Sharma
Summary: The popularity of microflow chemistry has significantly increased in the last 20 years, leading to a transition from macro-batch reactors to miniaturized flow devices among chemists. Microfluidics has established itself as not just a trend but a new, effective, and sustainable way of conducting chemistry in the field of organic chemistry, with continuous growth and evolution expected. This perspective highlights the use of innovative enhancing technologies applied to microflow reactors, as well as examples of complex integrated microsystems and scale-up technologies, showcasing microflow as a promising choice for the future.
Article
Chemistry, Organic
Liangliang Song, Zhenwei Lv, Yan Li, Kui Zhang, Erik V. Van der Eycken, Lingchao Cai
Summary: In this study, a Rh(III)-catalyzed C-H activation/annulation reaction was developed for the diversification of Lys-based peptides, yielding a range of peptide-isoquinolone conjugates. This method offers racemization-free conditions, high atom and step economy, excellent chemo- and site-selectivity, and broad substrate scope. Furthermore, the peptide-isoquinolone conjugates demonstrate good fluorescent properties and show potential antifungal activity against crop and forest pathogenic fungi, with a particular conjugate exhibiting superior activity compared to the positive control.
Article
Chemistry, Organic
Laura Y. Y. Vazquez-Amaya, Brecht Dootselaere, Gerardo M. M. Ojeda-Carralero, Serena Pillitteri, Johan Van der Eycken, Erik V. V. Van der Eycken, Upendra K. K. Sharma
Summary: Here, we report a one-pot aminoalkylation reaction of styrene derivatives with boronic acids and boronic acid pinacol esters. This reaction provides a mild and easily accessible method for the synthesis of complex secondary amines in moderate to high yields. Additionally, we demonstrate the activation of alkyl boronic acid derivatives by imines in a photoredox process for the first time, which serves as both substrate and Lewis base activator in the reaction. The applicability of this protocol is greatly enhanced by its successful adaptation to photoflow reactors.
Article
Chemistry, Organic
Monica Oliva, Viktoriia V. Chernobrovkina, Erik V. van der Eycken, Upendra Kumar Sharma
Summary: Photoredox catalysis has gained significant attention in the synthetic community due to its ability to form challenging C-C and C-heteroatom bonds under mild and sustainable conditions. Developing novel synthetic strategies and suitable technologies to overcome scale-up issues has become a primary focus. Continuous-flow reactors play a major role in increasing the efficiency and accessibility of photocatalyzed reactions. Recent interest in using boron species as radical precursors in photocatalyzed reactions has emerged, despite the challenges posed by the high oxidation potential of boronic acids. This Account highlights recent contributions to this field with a focus on applicability, selectivity, and scalability through continuous-flow methodology.
Article
Chemistry, Multidisciplinary
Chao Liu, Johan Van Der Eycken, Erik V. Van Der Eycken
Summary: A novel method was developed for transition metal-free N-S bond cleavage and subsequent C-N bond activation of Ugi-adducts. Diverse primary amides and a-ketoamides were prepared in a rapid, step-economic, and highly efficient manner in two steps. This strategy offers excellent chemoselectivity, high yield, and functional-group tolerance. Primary amides derived from the pharmaceuticals probenecid and febuxostat were successfully prepared. This method provides a new environmentally friendly pathway for the simultaneous synthesis of primary amides and a-ketoamides.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Arina Y. Obydennik, Alexander A. Titov, Anna V. Listratova, Tatiana N. Borisova, Irina L. Sokolova, Victor B. Rybakov, Erik V. Van der Eycken, Leonid G. Voskressensky, Alexey V. Varlamov
Summary: In this study, 1-substituted 1-ethynyl-2-vinyldi- and tetrahydroisoquinolines were successfully subjected to [3,3]-sigmatropic rearrangement under microwave irradiation at 150 degrees Celsius in toluene, in the presence of nucleophiles (DMAP, triphenylphosphine and tetrahydrothiophene), yielding pyrrolo[2,1-b][3]benzazepines with good yields. The replacement of toluene with acetonitrile directed the rearrangement towards the formation of 7,11b-dihydro-6H-pyrido[2,1-a]isoquinolines.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Organic
Alisa A. Nevskaya, Anna D. Zinoveva, Erik V. van der Eycken, Leonid G. Voskressensky
Summary: This paper provides a review on the synthesis methodologies and applications of different indolizine derivatives, including thienoindolizines and indolizino[8,7-b]indoles. Indolizine nucleus is a privileged scaffold of various natural and synthetic molecules with significant biological activity. Fused-indolizines, such as thienoindolizines and indolizinoindoles, have attracted great interest due to their antitumor, antimicrobial, and enzyme inhibitor activity. The study summarizes the approaches to the synthesis, properties, and application of various indolizine derivatives, with a focus on recent articles on indolizines and indolizino[8,7-b]indoles, as well as a general review on thienoindolizine derivatives.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Liangliang Song, Lingchao Cai, Lei Gong, Erik V. Van der Eycken
Summary: Copper-catalyzed enantioselective coupling reactions have been extensively studied for the rapid synthesis of chiral molecules. Despite progress in polar and radical mechanisms, the development of general and practical strategies for the regio-, enantio-, and diastereoselective assembly of stereogenic centers remains challenging. The integration of photocatalysis with asymmetric copper catalysis offers new reaction pathways and diverse chiral compounds, expanding the scope of radical chemistry. This review provides a summary of recent advances in photoinduced copper-catalyzed enantioselective coupling reactions, with a discussion on the mechanistic aspects.
CHEMICAL SOCIETY REVIEWS
(2023)
Review
Chemistry, Multidisciplinary
Alexey A. Festa, Olga A. Storozhenko, Leonid G. Voskressensky, Erik V. van der Eycken
Summary: The use of visible light-promoted chemistry in halogenation and halofunctionalisation reactions has significant impact.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Xianjun Xu, Liliang Huang, Eva Smits, Ling Zhong, Huangdi Feng, Erik V. Van der Eycken
Summary: A novel strategy for the synthesis of various N-alkenylisoquinolinones is reported, featuring broad functional group tolerance and good chemoselectivity. This strategy involves sequential palladium-catalyzed cyclization and C-4-O bond cleavage of oxazolidines to form carbon-carbon and carbon-oxygen double bonds. Additionally, the practical value of this method is explored by conducting a millimole reaction and utilizing palladium-catalyzed C-H arylation and visible-light-assisted photocatalyzed conversion of the cyclic enamide to valuable compounds.
NEW JOURNAL OF CHEMISTRY
(2022)
