Article
Chemistry, Applied
Bartosz Bisek, Wojciech Chaladaj
Summary: This study describes the Pd-catalyzed tandem cyclization/coupling of internal β-propargylic β-ketoesters with (hetero)aryl bromides. Two protocols are established to selectively produce either 2-benzylidene-dihydrofurans or 2-benzyl-furans. The proposed catalytic cycle involves oxidative addition, substitution of bromide with alkyne, rate-limiting anti-selective 5-exo-dig oxocyclization, deprotonation of the oxonium intermediate, and reductive elimination.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Sanghyup Seo, Donghyeon Kim, Hyunwoo Kim
Summary: The reductive cross-coupling of terminal alkenes and N-heterocyclic bromides was successfully demonstrated through ligand optimization of Pd and CuH catalysis. The optimized ligands for Pd and CuH catalysis, Briphos and DTB-DPPBz respectively, were further applied to gram-scale production of clathryimine B.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Lucia Veltri, Roberta Amuso, Tommaso Prestia, Paola Vitale, Bartolo Gabriele
Summary: In this study, a direct and multicomponent approach to synthesize important fused-ring heterocycles was reported. The reaction employs readily available building blocks and shows high yields of the desired products under mild conditions. The reaction proceeds through a sequence of ordered steps.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Raffaella Mancuso, Patrizio Russo, Melania Lettieri, Domenico Santandrea, Corrado Cuocci, Bartolo Gabriele
Summary: Polycyclic heterocyclic derivatives can be synthesized in one step by a carbonylative double cyclization approach, with yields ranging from 45% to 86%, showing promising potential for various applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Hayeon Kwak, Eunsu Kang, Jae Yeong Song, Geunhee Kang, Jung Min Joo
Summary: The development of modular approaches for heteroaromatic cores and substituents is crucial for drug candidates and organic functional materials. A new strategy involving the cyclization of heteroarenes tethered with alkynes through a norbornene bridge was developed. The Pd catalytic system transformed a variety of five-membered heteroarenes to the corresponding benzofused products, demonstrating its versatility in the annulation of (hetero)aromatic rings.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Yulia A. Antonova, Yulia Nelyubina, Sema L. Ioffe, Alexey Yu Sukhorukov, Andrey A. Tabolin
Summary: It was discovered that acylation of nitroalkylmalonates can produce substituted isoxazoline derivatives, with a high yield and wide substrate scope. A quick assembly of the isoxazoline ring starting from nitroalkenes and malonates was successfully developed, demonstrating the synthetic utility of the obtained products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Chengqiang Cao, Yi Yang, Xin Li, Yunxia Liu, Hui Liu, Zengdian Zhao, Lei Chen
Summary: The reaction, catalyzed by palladium, efficiently constructs two new bonds with high yields, while the alkene group is easily functionalized, leading to the formation of products with a unique structure that is difficult to synthesize.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ramon Arora, Jose F. Rodriguez, Andrew Whyte, Mark Lautens
Summary: A palladium-catalyzed strategy has been proposed for synthesizing unsymmetrically linked heterocycles within stereoselective tetrasubstituted olefins, with high yields and excellent stereoselectivities achieved using low catalyst loadings. Mechanistic studies suggest a syn-carbopalladation of the carbamoyl chloride followed by Pd-II-catalyzed cyclization of alkyne-tethered nucleophiles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Balazs L. Toth, Gergo Salyi, Attila Domjan, Orsolya Egyed, Attila Benyei, Zsombor Gonda, Zoltan Novak
Summary: The study reports a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds utilizing palladium-catalyzed ortho C-H activation reaction of aniline derivatives. The use of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allows mild reaction conditions, and feasibility has been demonstrated through over 50 examples.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Raffaella Mancuso, Alex De Salvo, Patrizio Russo, Aurelia Falcicchio, Nicola Della Ca, Leonardo Pantoja Munoz, Bartolo Gabriele
Summary: The PdI2/KI-catalyzed oxidative carbonylation of 4-(2-aminophenyl)-3-yn-1-ols selectively produces dihydrofuroquinolinone derivatives in fair to high yields (60%-89%) and excellent turnover numbers (180-267 mol of product per mol of Pd) over 19 examples. This reaction involves the catalytic construction of two rings and three new bonds in one step, providing high value added fused heterocyclic structures from readily available materials.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jessica C. Bieniek, Boris Mashtakov, Dieter Schollmeyer, Siegfried R. Waldvogel
Summary: This study presents an electrocatalytic method using hypervalent iodine(III) as a mediator to synthesize 1H-N-aryl-3,4-dihydroquinolin-2-ones by C-N bond formation. The method features a low catalyst loading, recycling of the solvent, and is a sustainable alternative to conventional approaches.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Yanke Hao, Pan Zhou, Kaikai Niu, Hongjian Song, Yuxiu Liu, Jingjing Zhang, Qingmin Wang
Summary: The study presents a method for synthesizing indole- and pyrrole-fused seven-membered nitrogen heterocycles through acid-base switchable cyclization reactions, which can construct two different kinds of seven-membered rings in one step from the same starting material without the need for a transition-metal catalyst.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Tsunehisa Hirashita, Harue Watanabe, Yuki Harada, Hideaki Kurabayashi, Yukinobu, Yamashita, Shiyogo Oizumi, Shuki Araki
Summary: The Pd-catalyzed bromination of mesoionic 1,3-diphenyltetrazolium-5-olate was developed, with the 4-nitrogen atom acting as a directing group. Specific conditions were used to achieve bromination, demonstrating the role of the palladium catalyst and bromine reagent in the reaction.
Article
Chemistry, Organic
Xu-Heng Yang, Jian Huang, Fang Wang, Zhuoliang Liu, Yujiao Li, Cheng-an Tao, Jianfang Wang
Summary: A synthetic strategy based on sequential application of aza-Claisen rearrangement, C-H functionalization, C-N coupling, and cyclization has been developed for the synthesis of various medium-sized N-heterocycles of pharmaceutical relevance, providing a highly efficient synthesis of N-heterocycles of different ring sizes in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Zipeng Wang, Tongxiang Cao, Shifa Zhu
Summary: The coupling reaction of enynal and enynol catalyzed by gold has been achieved by selectively steering two transient vinyl-gold intermediates, showing high atom economy and good tolerance of functional groups, with the reactivity being determined by the in situ formed vinyl-gold.
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)
Article
Biochemical Research Methods
Thi Yen Hang Bui, Peter Dedecker, Luc Van Meervelt
Summary: rsCherryRev1.4 is a reversibly photoswitchable variant of mCherry with improved properties compared to its precursor. The crystal structure of rsCherryRev1.4 revealed dimerization through disulfide bonding, which was strongly influenced by the presence of Cys24. This finding suggests the potential for developing redox sensors based on controlled dimerization in fluorescent proteins.
ACTA CRYSTALLOGRAPHICA SECTION F-STRUCTURAL BIOLOGY COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Bing-Yu Li, Kexin Su, Luc Van Meervelt, Steven H. L. Verhelst, Ermal Ismalaj, Wim M. De Borggraeve, Joachim Demaerel
Summary: SuFEx chemistry enables rapid and flexible assembly of linkages around a S-VI core by replacing fluoride at an electrophilic sulfur(VI). Thiazyl trifluoride (NSF3) gas is introduced as an excellent parent compound and SuFEx hub to efficiently synthesize mono- and disubstituted fluorothiazynes. These results provide valuable insights into the versatility of these understudied sulfur functionalities, paving the way for future applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
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
Biochemistry & Molecular Biology
Thi Yen Hang Bui, Elke De Zitter, Benjamien Moeyaert, Ludovic Pecqueur, Bindu Y. Srinivasu, Anastassios Economou, Marc Fontecave, Luc Van Meervelt, Peter Dedecker, Branden Pedre
Summary: This article investigates the mechanism of fluorescence loss in the reversibly switchable monomeric Cherry (rsCherry) and its ancestor mCherry. It is found that the gradual loss of red fluorescence in the dark is caused by structural changes in the chromophore. This study provides new insights into a novel process occurring within fluorescent proteins, enhancing the chemical diversity and versatility of these molecules.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Physical
Yassine Laamari, Abdoullah Bimoussa, Mourad Fawzi, Ali Oubella, Taoufik Rohand, Luc Van Meervelt, My Youssef Ait Itto, Hamid Morjani, Aziz Auhmani
Summary: A series of novel compounds containing thymol were synthesized and their structures were confirmed. The compounds demonstrated moderate to high cytotoxicity against four human cancer cell lines. Particularly, compound 4b showed significant cytotoxicity and induced apoptosis in HT-1080 and A-549 cells. Evaluation techniques such as staining and flow cytometry were used to assess the effects on cell cycle and apoptosis.(c) 2023 Elsevier B.V. All rights reserved.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
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
Felien Reniers, Stijn Anthonissen, Luc Van Meervelt, Wim Dehaen
Summary: This study presents a three-step synthetic pathway for the synthesis of fully decorated 8-azapurines, with a special focus on 6-alkyl derivatives. A diverse library of 8-azapurines was successfully obtained through interrupted CuAAC, oxidation, and cyclization reactions using various alkynes, azides, and amidines. Additionally, postfunctionalization reactions were demonstrated for selected substrates.
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
Materials Science, Multidisciplinary
Jianjun Huang, Flip de Jong, Davita Martina Elisa van Raamsdonk, Jonathan Vandenwijngaerden, Akane Inoue, Daniel Escudero, Luc Van Meervelt, Mark van der Auweraer, Wim Dehaen
Summary: A new family of unsymmetrical boron chromophores, BOPAM, has been developed through a one-pot, three-step reaction with high efficiency and broad substrate tolerance. Some of the BOPAM dyes exhibit interesting photophysical properties with fluorescence quantum yields up to 0.98 in toluene. Tailored molecular design guided by computational investigations allows precise tuning of their emissive properties.
ADVANCED OPTICAL MATERIALS
(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)
Article
Multidisciplinary Sciences
Nadeem Abad, Fares Hezam Al-Ostoot, Sajda Ashraf, Karim Chkirate, Majed S. Aljohani, Hussam Y. Alharbi, Shafeek Buhlak, Mohamed El Hafi, Luc Van Meervelt, Basheer M. Al-Maswari, El Mokhtar Essassi, Youssef Ramli
Summary: Drug design is a constantly evolving field where researchers strive to improve their understanding of molecular interactions and develop innovative techniques for creating effective and safe medications. This article reports the synthesis and characterization of a novel triazolequinoxalin molecule (TZQ) through various spectroscopic and crystallographic methods.
