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Palladium-catalyzed cross-coupling of (di)chloropyrazines with phosphorus pronucleophiles in the presence of a base gave the phosphorylated pyrazines in 81-95% yields. Based on this methodology a series of appropriately functionalized pyrazines was prepared as potential extractants of trivalent cations from highly acidic nuclear waste. A few hydrophilic derivatives exhibited a very good selectivity for Am(3+) over Eu(3+) with separation factors up to 40 at pH 1 at 0.01 mol L(-1) ligand concentration.
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http://dx.doi.org/10.1039/c2ob25787d | DOI Listing |
ChemSusChem
September 2025
Leibniz Institute for Catalysis e.V., Albert-Einstein-Straße 29a, 18059, Rostock, Germany.
The palladium-catalyzed Suzuki-Miyaura cross coupling reaction to forge carbon-carbon bonds fundamentally changes the practice of organic synthesis. Herein an isolated palladium catalyst supported on polymeric carbon nitride (Pd/PCN) for efficient cross coupling of bromobenzene and phenylboronic acid at room temperature is reported. It is demonstrated that the Pd/PCN catalyst with a 2 wt% Pd loading achieves the highest mole-specific activity.
View Article and Find Full Text PDFOrganometallics
June 2025
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48104, United States.
This article describes a detailed investigation of the palladium-catalyzed coupling of aryl (pseudo)halides (ArX) with MSCF to form aryl trifluoromethylthioethers (ArSCF). Mechanistic organometallic studies are used to interrogate two key elementary steps of the catalytic cycle: (1) transmetalation of Pd(Ar)(X) complexes with MSCF and (2) Ar-SCF bond-forming reductive elimination. These studies reveal that tetramethylammonium trifluoromethylthiolate, NMeSCF, exhibits a combination of fast kinetics and high chemoselectivity for transmetalation.
View Article and Find Full Text PDFMolecules
August 2025
Medicinal Biotechnology Department, Sirius University of Science and Technology, Olimpiyskiy Ave. 1, 354340 Sirius, Krasnodar Region, Russia.
Several approaches to the synthesis of risdiplam, a pharmacologically relevant pyridopyrimidinone derivative, have been recently reported. However, most of these routes rely exclusively on palladium-catalyzed, cross-coupling reactions and involve low-yielding intermediates, which limit their scalability and complicate impurity control. In this work, we present a five-step, straightforward route to risdiplam, utilizing ethyl 2,8-dimethylimidazo[1,2-]pyridazine-3-carboxylate-an accessible and cost-effective building block previously developed by our research group-as a starting material.
View Article and Find Full Text PDFJ Org Chem
August 2025
Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Botanic Garden, Howrah 711103, India.
A range of (,)-1,4-diarylbutadienes has been efficiently achieved through a Pd-catalyzed decarboxylative cross-coupling of various 2,4-dienoic acids with diverse (hetero)aryl halides, such as bromides, chlorides, and iodides. This protocol successfully produces the corresponding 1,4-diarylbutadiene cross-coupled products in high yields across a large range of substrates (68 examples), demonstrating compatibility with various sensitive functional groups, including heterocycles. A catalytic amount of silver salt was used as a cocatalyst in this approach, replacing the stoichiometric amounts utilized in earlier reports.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, China.
A palladium-catalyzed domino Heck/cross-coupling reaction of alkene-tethered aryl iodides with β-chloroenones is reported. This reaction enables the formation of one C-O bond and two C-C bonds to construct bisheterocycles in a single operation an intramolecular carbopalladation, followed by a carbene-based cross-coupling with β-chloroenones as a non-diazo carbene precursor, providing an efficient method for synthesizing furan-linked dihydrobenzofurans/oxindoles in yields up to 98%.
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