The aza-Michael addition of 1,2,3,6-tetrahydrophthalimide with symmetrical fumaric esters has been performed efficiently in a solvent-free system at 100 °C and using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a base in the presence of tetrabutylammonium bromide (TBAB). The products were obtained in good to high yields within 2.5-7.0 h. This reaction worked well on linear alkyl fumarates and was not effective with nonlinear alkyl fumarates. Although the reaction was also applicable to acrylates such as n-butyl acrylate, methacrylates and crotonates were not suitable Michael acceptors for this reaction.
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http://dx.doi.org/10.3390/molecules15107353 | DOI Listing |
Org Biomol Chem
January 2025
Department of Chemistry, Faculty of Arts and Sciences, Amasya University, Amasya, Turkey.
Herein, a new metal-free, molecular chlorine-free, environmentally friendly, atom-economical, short time, inexpensive and simple operation method with mild reaction conditions for chlorination of alkenes, cyclic alkenes, ,-unsaturated carbonyl compounds, heteroaromatics, and natural products was reported with up to 96% yields using trichloroisocyanuric acid (TCCA) as the electrophilic chlorine source and TBACl as the nucleophilic chlorine source. It was demonstrated with bicyclic alkene benzonorbornadiene that regioselective chlorobromination and dibromination reactions can be carried out through TCCA/TBABr redox reactions, where TCCA acts as an oxidant in the presence of TBABr. The structures of the redox products were confirmed as a result of control experiments conducted with the newly presented DBI/TBACl and DBI/TBABr halogenation pairs.
View Article and Find Full Text PDFTetrahedron
February 2025
Department of Chemistry, Western Washington University, Bellingham, WA 98225 (USA).
Beta-hydroxy ketones can be reduced using a sequence of ruthenium-catalyzed silyl etherification followed by tetrabutylammonium fluoride (TBAF) promoted intramolecular hydrosilylation. Switching from TBAF to tetrabutylammonium difluorotriphenylsilicate (TBAT), even without first forming the silyl ether, gave cyclic dioxasilinane products. These somewhat sensitive compounds could be isolated pure by column chromatography using florisil as the stationary phase.
View Article and Find Full Text PDFMolecules
December 2024
Institute of Organic and Analytical Chemistry (ICOA UMR 7311), CNRS, University of Orleans, F-45067 Orléans, France.
The emergence of RNA viruses driven by global population growth and international trade highlights the urgent need for effective antiviral agents that can inhibit viral replication. Nucleoside analogs, which mimic natural nucleotides, have shown promise in targeting RNA-dependent RNA polymerases (RdRps). Starting from protected 5-iodouridine, we report the synthesis of -substituted-(1,3-diyne)-uridines nucleosides and their phosphoramidate prodrugs.
View Article and Find Full Text PDFMolecules
December 2024
Department of Chemistry, University of Bari, Via Orabona 4, 70126 Bari, Italy.
Optoelectronic devices combining single-layer graphene (SLG) and colloidal semiconducting nanocrystal (NC) heterojunctions have recently gained significant attention as efficient hybrid photodetectors. While most research has concentrated on systems using heavy metal-based semiconductor NCs, there is a need for further exploration of environmentally friendly nanomaterials, such as CuS. Chemical ligands play a crucial role in these hybrid photodetectors, as they enable charge transfer between the NCs and SLG.
View Article and Find Full Text PDFNanomaterials (Basel)
December 2024
Leibniz-Institut für Polymerforschung Dresden e.V., Hohe Str. 6, 01069 Dresden, Germany.
Understanding the interplay between the molecular structure of the ionic liquid (IL) subunit, the resulting nanostructure and ion transport in polymerized ionic liquids (PILs) is necessary for the realization of high-performance solid-state electrolytes required in various advanced applications. Herein, we present a detailed structural characterization of a recently synthesized series of acrylate-based PIL homopolymers and networks with imidazolium cations and chloride anions with varying alkyl spacer and terminal group lengths designed for organic solid-state batteries based on X-ray scattering. The impact of the concentrations of both the crosslinker and added tetrabutylammonium chloride (TBACl) conducting salt on the structural characteristics is also investigated.
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