Sonogashira coupling of phenylacetylene with iodobenzene has been studied in the presence of metallic Rh nanoparticle catalysts and found to occur via a surface-mediated heterogeneous route. Homogeneous catalytic processes due to Rh species that may leach into solution were barely detectable within the sensitivity of our experiments. Moreover, larger (8 nm) nanoparticles were found to be much better catalysts than very small ones (2 nm), which is consistent with the hypothesis that steric limitations adversely affect the efficiency of the latter.
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http://dx.doi.org/10.1039/b912833f | DOI Listing |
ACS Nano
January 2025
Department of Chemistry and Applied Biosciences, Institute for Chemical and Bioengineering, ETH Zurich, 8093 Zurich, Switzerland.
Single-atom heterogeneous catalysts (SACs) are potential, recoverable alternatives to soluble organometallic complexes for cross-coupling reactions in fine-chemical synthesis. When developing SACs for these applications, it is often expected that the need for ligands, which are essential for organometallic catalysts, can be bypassed. Contrary to that, ligands remain almost always required for palladium atoms stabilized on commonly used functionalized carbon and carbon nitride supports, as the catalysts otherwise show limited activity.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin, 300384, China.
Herein, we report an enantioselective Pd/Cu-catalyzed sequential Heck/Sonogashira coupling reaction of electron-rich enamides with terminal alkynes as substrates. This transformation proceeds smoothly to afford 3-propargyl isoindolinone derivatives bearing quaternary stereogenic centers in moderate to good yields (43-77% yield) and good to excellent enantioselectivity (up to 93% ee). Functional groups such as halogen atoms (F, Cl, and Br), thienyl, and silyl moieties are tolerated well.
View Article and Find Full Text PDFInt J Mol Sci
December 2024
Department of Organic Chemistry, Eötvös Loránd University (ELTE), Pázmány P. Sétány 1/A, H-1117 Budapest, Hungary.
Our ongoing research focuses on the development of new imipridone derivatives. We aim to design compounds that can completely and selectively eradicate cancer cells after relatively short treatment. We have synthetized systematically designed novel hybrids and evaluated their antiproliferative activity against PANC-1 and Fadu cell lines.
View Article and Find Full Text PDFJ Org Chem
December 2024
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8 Canada.
Org Lett
December 2024
Leibniz-Institut für Katalyse e.V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany.
Herein, we developed a mild and efficient palladium-catalyzed carbonylative Sonogashira coupling of aryl thianthrenium salts with aliphatic alkynes and benzyl acetylene toward alkynones and furanones. Various desired products were prepared in good yields with broad functional group tolerance including the bromide group. In the case of using benzyl acetylene, the corresponding furanones can be obtained in good yields under the same conditions with two molecules of CO inserted.
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