Facile conversion of α,β-unsaturated aldehydes and ketones into highly substituted arenes via a base-mediated, completely regioselective, air-oxidative [3 + 3] benzannulation reaction with readily available 4-sulfonylcrotonates or 1,3-bisphenylsulfonylpropene is reported. The reaction can also be carried out as a one-pot, three-component operation using 4-bromocrotonates, aryl sulfinates, and cinnamaldehyde. This open-flask, metal-free reaction does not require anhydrous solvents, proceeds under mild conditions, and uses atmospheric oxygen as the oxidant to afford high yields of the 3-(arylsulfonyl)benzoic acid esters.
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http://dx.doi.org/10.1021/acs.orglett.5b00318 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
USTC: University of Science and Technology of China, Department of Chemistry, No. 96 Jinzhai Road, 230026, Hefei, CHINA.
The synthesis of metal-organic frameworks (MOFs) by low energy input has been a long-term target for practical applications yet remains a great challenge. Herein, we developed a low-energy MOF growth strategy at a temperature down to 50 °C by simply introducing seeds into the reaction system. The MOFs are continuously grown on the surface of the seeds at a growth rate dozens of times higher than that of conventional solvothermal synthesis at low temperature, while the resulting MOFs possess high crystallinity, porosity, and stability similar to solvothermal seeds.
View Article and Find Full Text PDFJ Biol Inorg Chem
December 2024
Izmir International Biomedicine and Genome Institute, Dokuz Eylul University, 35340, Izmir, Turkey.
As novel promising anticancer candidates, the piano-stool type complexes of ruthenium, [RuCl(η-p-cymene)(N,S-L)]PF, K-, were synthesized from the reaction of the substituted benzo[b]thiophene based thiosemicarbazone ligands (L) with [{RuCl(η-p-cymene)}(μ-Cl)]. All complexes were fully characterized using elemental analysis, and spectroscopic methods such as FT-IR and H NMR. The molecular masses of the complexes were proved by MALDI-TOF analysis.
View Article and Find Full Text PDFOrg Lett
January 2025
Heilongjiang Provincial Key Laboratory of Surface Active Agent and Auxiliary, Technology Innovation Center of Industrial Hemp for State Market Regulation, Institute of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, P. R. China.
Part belt oxygen-functionalized pillar[6,10]arenes are synthesized by step cyclization. An oxygen-substituted tetramer and hexamer have been prepared to construct the O3 pillar[6]arene via a hexamer cyclization reaction and the O6 pillar[10]arene through a [4 + 1+4 + 1] cyclization reaction. X-ray crystallographic studies reveal that both macrocycles have a large cavity and indicate that the part belt oxygen-functionalized pillar[6,10]arenes have both similar cyclic structures and certain differences in configuration compared to pillararene.
View Article and Find Full Text PDFBeilstein J Org Chem
December 2024
Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), CNRS-Université de Strasbourg (UMR 7504), F-67034 Strasbourg, France.
The high potential of non-covalent arene-fluoroarene intermolecular interactions in the design of liquid crystals lies in their ability to strongly promote self-assembly, improve the order and stability of the supramolecular mesophases, and enable tuneability of the optical and electronic properties, which can potentially be exploited for advanced applications in display technologies, photonic devices, sensors, and organic electronics. We recently successfully reported the straightforward synthesis of several mesogens containing four lateral aliphatic chains and derived from the classical triphenylene core self-assembling in columnar mesophases based on this paradigm. These mesogenic compounds were simply obtained in good yields by the nucleophilic substitution (SFAr) of various types of commercially available fluoroarenes with the electrophilic organolithium derivatives 2,2'-dilithio-4,4',5,5'-tetraalkoxy-1,1'-biphenyl (2Li- ).
View Article and Find Full Text PDFChempluschem
December 2024
Budapest University of Technology and Economics, Department of Chemical and Environmental Process Engineering, Muegyetem rkp. 3., 1111, Budapest, HUNGARY.
The palladium-catalyzed aminocarbonylation is one of the most effective methods for the synthesis of carboxamides having great importance. Replacing fossil-based organic solvents in this routinely used catalytic protocol with biomass-derived media is crucial for developing environmentally safe alternatives and towards sustainability considerations. In this study, the open-chain derivatives of bio-originated substance g-valerolactone i.
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