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A Pd-catalyzed multicomponent cross-coupling of allyl esters with alkyl bromides to synthesize allylic sulfones by using KSO as a connector is first reported. The reaction displays a broad range of substrate generality along with excellent functional group compatibility and produces the products with high regioselectivity (only E). Furthermore, the biologically active molecules with a late-stage modification, including aspirin, menthol, borneol, and estrone, are also highly compatible with the multicomponent cross-coupling reaction. Mechanistic studies indicate that the process of SO insertion into the C-Pd bond was involved in this transformation.
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http://dx.doi.org/10.1021/acs.orglett.3c02066 | DOI Listing |
Org Lett
July 2025
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Pharmacy, and School of Chemical Science and Technology, Yunnan University, Kunming 650500, P. R. China.
The selective assembly of azahelical structures is not trivial and constitutes a pivotal challenge in material science and organic synthesis. Described herein is a facile and modular approach to construct diverse functionalized 1-azahelicenes through the combination of a Pd/NBE-catalyzed three-component cross-coupling reaction with an alkyne benzannulation process. The appealing features of this method include readily accessible starting materials, step economy, good functional-group tolerance, and a scale-up potential.
View Article and Find Full Text PDFMolecules
June 2025
Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania.
In this study, novel fluorescent 5-aryl-2-styryl-3-indole derivatives were efficiently synthesized from 4-bromophenylhydrazine hydrochloride using the microwave-accelerated one-pot technique, which includes Fischer synthesis, Suzuki cross-coupling, and Knoevenagel condensation. The structural assignments of the synthesized compounds were based on H, C, N, and F NMR; IR spectroscopy; and HRMS spectral data. The optical properties of the newly obtained styryl-indole dyes were studied using UV-vis and fluorescence spectroscopy, which clearly demonstrated that the derivatives substituted with electron-donating or -withdrawing groups exhibited varying emission shifts and quantum yields ranging from negligible to high.
View Article and Find Full Text PDFChem Sci
July 2025
Institute of Functional Material Chemistry, Faculty of Chemistry, Northeast Normal University Changchun 130024 P. R. China
Three-component coupling reactions represent a potent approach for synthesizing complex products. Radical-initiated three-component coupling reactions hold significant promise in synthetic chemistry but are often challenged by the high reactivity of radical species and the complex coordination environment of transition metal catalysts. Herein, we employed density functional theory (DFT) and molecular dynamics (AIMD) simulations to investigate the mechanism of three-component olefin difunctionalization.
View Article and Find Full Text PDFNat Commun
May 2025
Shenzhen Key Laboratory of Cross-Coupling Reactions, Southern University of Science and Technology, 518055, Shenzhen, China.
Transition-metal-catalysed asymmetric multicomponent reactions with two similar substrates often suffer from the lack of strategies to control the chemo-, regio-, and stereoselectivity of these substrates due to the close similarity in the chemical structures and properties of each reagent. Here, we describe a Cu(I)-catalysed asymmetric radical 1,2-carboalkynylation of two different terminal alkynes and alkyl halides with high chemo-, regio-, and stereoselectivity by using sterically bulky chiral tridentate anionic N,N,P-ligands and modulating alkynes with different electronic properties to circumvent above-mentioned challenges. This method features good substrate scope, high functional group tolerance of two different terminal alkynes, and diverse alkyl halides, providing universal access to a series of useful axially chiral 1,3-enyne building blocks.
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May 2025
State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, China.
The arylpyridylmethylamine motif is a privileged scaffold in drug discovery. However, rapidly creating these valuable molecules with structural diversity by directly leveraging readily available, yet simple chemical feedstocks remains a challenge. Herein, we describe a versatile and modular photochemical method for the straightforward construction of arylpyridylmethylamine skeleton utilizing widely accessible starting materials, including amines, aldehydes, and pyridines.
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