The room temperature 1,3-dipolar cycloaddition reactions of the boron azide, Cy2BN3 with the electron-poor acetylenes RCO2C≡CCO2R, EtC≡CCOMe and HC≡CP(=O)Ph2 afforded new 1,2,3-triazoles. In the case of RCO2C≡CCO2R, a new macrocyclic product was isolated with loss of the R group.
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http://dx.doi.org/10.1039/c3dt00068k | DOI Listing |
Org Lett
January 2025
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
1,1-Difluoroallenes underwent regioselective [2 + 2] and [3 + 2] cycloadditions with aldehydes using Au(I) catalysts. An AuCl catalyst enabled an α,β-selective [2 + 2] cycloaddition of 1,1-difluoroallenes, yielding ()-3-alkylidene-2,2-difluorooxetanes. Conversely, an AuCl(IPr)-AgSbF catalyst facilitated an α,γ-selective [3 + 2] cycloaddition, followed by dehydrofluorination to produce aromatized 2-fluorofurans.
View Article and Find Full Text PDFThe carbon dioxide (CO) capture and utilization strategy has emerged as an innovative and multifaceted approach to counteract carbon emissions. In this study, a highly porous muffin polyhedral barium (Ba) ̵ organic framework (BaTATB; HTATB = 4,4',4″--triazine-2,4,6-triyl-tribenzoic acid) was synthesized solvothermally. The three-dimensional honeycomb pore architectures were densely populated with Lewis acidic Ba(II) metal sites and basic nitrogen-rich triazines.
View Article and Find Full Text PDFAnal Bioanal Chem
January 2025
School of Food Science and Engineering, Shaanxi University of Science and Technology, Xi'an, 710021, China.
Matrix effects pose a significant challenge in food analysis for the quantitative analysis of complex food samples. Herein, a novel magnetic covalent organic framework nanocomposite and the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction-based stable isotope labeling (SIL) method were presented for highly selective and sensitive detection of steroid hormones in food samples using HPLC-MS/MS. The nanocomposite, FeO@TAPB-COF, with a core-shell structure exhibited high adsorption capacities for steroid hormones.
View Article and Find Full Text PDFOrg Lett
January 2025
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 211800, China.
A palladium-catalyzed tandem reaction of 1-(2-iodophenyl)-3-arylprop-2-yn-1-ones and 1-(2-azidophenyl)propargyl ethers is developed to provide the rapid construction of a fused polycyclic indenone-indole scaffold under mild conditions. The reaction proceeds via a highly ordered process involving Sonogashira coupling, propargyl-allenyl isomerization, allene-azide cycloaddition, denitrogenation, and diradical coupling. The proposed reaction mechanism is supported by experimental and computational studies.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Materials Science and Engineering, Institute of Science Tokyo, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.
A series of 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) derivatives with various heterocyclic moieties, including pyridine, carbazole, indole, and benzothiadiazole, was newly synthesized through a [2 + 2] cycloaddition-retroelectrocyclization reaction. Symmetric electron-rich 1,3-butadiynes with end-capped heterocyclic substituents were reacted with tetracyanoethylene (TCNE), yielding the target TCBD products in 60-80% yields under ambient or mild heating conditions. The thermal stability and optical and electrochemical properties of both 1,3-butadiyne precursors and the corresponding TCBD derivatives were investigated by using thermogravimetric analysis (TGA), UV-vis spectroscopy, and cyclic voltammetry (CV).
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