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A palladium-catalyzed carbon-carbon bond activation-initiated reaction of 2-(3-phenyloxiran-2-yl)benzonitriles with arylboronic acids is reported. Multiple chemical bonds were cleavaged and reconstructed via β-carbon elimination in this reaction, enabling the construction of valuable benzo-fused dipyrromethenes that are difficult to prepare by other methods. Additionally, a series of benzannulated boron dipyrromethenes are synthesized and show practical significance in terms of expanding the applications and types of fluorescent materials. The proposed mechanism is supported by preliminary mechanistic experiments.
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http://dx.doi.org/10.1021/acs.orglett.0c02478 | DOI Listing |
Chem Commun (Camb)
August 2025
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
A novel palladium-catalyzed carboetherification reaction of β,γ-unsaturated ketoxime with -dihaloolefin has been developed. This process offers an efficient route for the assembly of isoxazoline-linked benzofuran/indole bis-heterocycles in moderate to good yields. The scalability of the reaction and subsequent transformations of the products highlight the synthetic potential of this developed method.
View Article and Find Full Text PDFNat Commun
July 2025
Instituto Universitario de Tecnología Química, CSIC-UPV, Universitat Politècnica de València, Valencia, Spain.
The rapid increase in atmospheric CO levels due to industrialization underscores the urgent need for innovative carbon valorization strategies. Photocatalytic CO reduction presents a sustainable solution; however, conventional systems suffer from inefficient charge separation and limited product applicability. Herein, a green and scalable tandem strategy is developed by integrating S-scheme photocatalysis with palladium-catalyzed carbonylation.
View Article and Find Full Text PDFOrg Lett
August 2025
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
A palladium-catalyzed tandem difunctional carbonylation of 1,3-enynes with fluoroalkyl halides and water has been developed, enabling efficient one-step access to fluoroalkylated butenolides. The method exhibits a broad substrate scope, high chemo- and regioselectivity, and good functional group tolerance. Mechanistic studies support a Pd/Cu-cooperative pathway involving radical addition and carbonylative cyclization.
View Article and Find Full Text PDFChem Sci
August 2025
Otto Diels-Institut für Organische Chemie, Christian-Albrechts Universität zu Kiel Otto-Hahn-Platz 4 Kiel 24118 Germany
In this study, we describe a direct palladium-catalyzed tandem β-C(sp)-H olefination/lactonization strategy for the one-step synthesis of γ-alkylidene lactones. The reaction is enabled by an -acyl sulfonamide ligand and utilizes readily available and inexpensive carboxylic acids and styrenes as coupling partners, enabling the efficient construction of structurally diverse γ-alkylidene lactones through the consecutive functionalization of three C-H bonds. Notable highlights include excellent functional group tolerance and derivatization of the resulting γ-alkylidene lactones to obtain various synthetically useful motifs.
View Article and Find Full Text PDFOrg Biomol Chem
July 2025
School of Chemistry and Chemical Engineering, Hainan University, Haikou, 570228, China.
1-Indanones represent a significant class of organic compounds commonly found in many bioactive and functional materials. In this work, we reported an efficient method for their preparation. Mediated by a palladium catalyst, -vinyl benzoic acids could undergo reductive cyclization in the presence of readily available formic acid, producing the corresponding 1-indanones in good to high yields.
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