In situ complexation of palladium acetate by a monolayer of a bipyridine derivative at a graphite/liquid interface has been observed using scanning tunneling microscopy.
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Pd-Catalyzed Asymmetric Hydrogenolysis Rearrangement of Allylic Esters to Access Axially Chiral Olefins.
Angew Chem Int Ed Engl
January 2025
School of Chemistry, Dalian University of Technology, Dalian, 116024, P. R. China.
The Pd-catalyzed asymmetric hydrogenolysis rearrangement of allylic acetates using (s-Bu)BHK has been described, achieving the synthesis of axially chiral alkylidene cycloalkanes with excellent enantioselectivities (up to 99 % ee) and a wide substrate scope (30 examples of cyclohexanes and cyclobutanes). To the best of our knowledge, this is the first time to achieve synthesis of axially chiral olefins via asymmetric hydrogenolysis of allylic acetates. This methodology not only offers a novel synthetic pathway for non-atropisomeric axially chiral structures but also highlights the potential of asymmetric hydrogenolysis as a powerful tool in synthetic organic chemistry.
View Article and Find Full Text PDFCombined Kinetic and Computational Analysis of the Palladium-Catalyzed Formylation of Aryl Bromides.
ACS Catal
January 2025
Molecular Sciences Research Hub, Imperial College London, 82 Wood Lane, Shepherds Bush, London W12 0BZ, U.K.
Aryl aldehydes are key synthetic intermediates in the manufacturing of active pharmaceutical ingredients. They are generated on scale (>1000 kg) through the palladium-catalyzed formylation of aryl bromides using syngas (CO/H). The best-in-class catalyst system for this reaction employs di-1-adamantyl--butylphosphine (cataium A), palladium(II) acetate, and tetramethylethylenediamine.
View Article and Find Full Text PDFUnlocking the Nucleophilic Functionalization Potential of a Natural Asphalt: Grafting a Pd(0)-Diethanolamine Complex as a Recyclable Catalyst for Upgrading Biaryl Synthesis.
Langmuir
January 2025
Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran.
Article Synopsis
- This study presents a new method for upgrading natural asphalt into a catalyst through a process called metal-free sonobromination.
- The method involves creating a palladium complex on natural asphalt, which is then used as a recoverable catalyst in the Suzuki reaction for synthesizing biphenyl derivatives.
- The process is environmentally friendly, uses a green solvent, and showcases the potential for sustainable materials development from renewable resources.
Synthesis, Reactivity and Aromatic Characteristics of Porphyrinoids Derived from -Alkylcarbaporphyrin-2-Carbaldehydes: Isolation of Nickel(II) and Palladium(II) Complexes, Weakly Diatropic 21-Oxycarbaporphyrins and Strongly Aromatic Trioxycarbaporphyrins.
J Org Chem
January 2025
Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, United States.
Acid catalyzed condensation of -alkyltripyrranes with trialdehydes derived from 1,3-cyclopentadiene or methyl-1,3-cyclopentadiene, followed by oxidation with aqueous ferric chloride solutions, gave 23-alkyl-21-carbaporphyrin-2-carbaldehydes in 22-27% yield together with weakly aromatic oxycarbaporphyrins. The carbaporphyrins reacted with palladium(II) acetate or nickel(II) acetate to give organometallic complexes but in both cases alkyl group migration took place to generate 21-alkyl derivatives. Although this type of reactivity had been observed previously for palladium complexes, this is the first time the phenomenon has been seen in nickel(II) carbaporphyrins.
View Article and Find Full Text PDFIntramolecular C-H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds.
Beilstein J Org Chem
December 2024
Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan.
The C-H arylation of 2-quinolinecarboxyamide bearing a C-Br bond at the -aryl moiety is carried out with a palladium catalyst. The reaction proceeds at the C-H bond on the pyridine ring adjacent to the amide group in the presence of 10 mol % Pd(OAc) at 110 °C to afford the cyclized product in 42% yield. The yield is improved to 94% when the reaction is performed with PPh as a ligand of palladium.
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