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Palladium-catalyzed intramolecular aerobic oxidative cross-coupling of BH/CH between -carborane and arenes.
Chem Sci
January 2025
Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences Shanghai 200032 China
An efficient Pd-catalyzed regioselective intramolecular aerobic oxidative dehydrocoupling of BH/CH between -carborane and arenes has been achieved with the construction of a series of five-, six- and seven-membered rings under mild reaction conditions. Control experiments indicate that B-H activation proceeds preferentially over the aryl C-H. These new polyarene-carborane conjugates have potential applications in materials as demonstrated by pyrene fused -carborane that exhibits unique dual-phase emission, intramolecular charge transfer (ICT), and aggregation-induced emission (AIE) properties.
View Article and Find Full Text PDFLigand-free palladium-catalyzed synthesis of 3-(2,2-dialkyl-2-chromen-4-yl)-2-phenylimidazo[1,2-]pyridine derivatives: molecular docking investigation of their potential as DNA gyrase inhibitors and evaluation of their antibacterial activities.
RSC Adv
January 2025
ICMR-Regional Medical Research Centre, Department of Health Research, Ministry of Health & Family Welfare, Govt. of India Bhubaneswar 751023 Odisha India.
Palladium-catalyzed reactions between imidazo[1,2-]pyridine derivatives and 4-bromo-2,2-dialkyl-substituted 2-chromenes under microwave irradiation at 100 W, 120 °C for 20-30 min provided a series of new 3-(2,2-dialkyl-2-chromen-4-yl)-2-phenylimidazo[1,2-]pyridine derivatives in good to excellent yields. The structures of the synthesized compounds were confirmed through spectroscopic techniques (NMR and HRMS). The X-ray single-crystal structure of compound 16e was also determined.
View Article and Find Full Text PDFPalladium-Catalyzed Modular Synthesis of Thiophene-Fused Polycyclic Aromatics via Sequential C-H Activation.
Org Lett
January 2025
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. China.
A palladium-catalyzed Catellani-type [2+2+2] annulation reaction of aryl iodides, bromothiophenes, and norbornadiene, which proceeds via a tandem Heck coupling/double C-H bond activation and retro-Diels-Alder pathway to access thiophene-fused polyaromatics, is reported. The key feature of this protocol represents a NBD/NBE retaining annulation.
View Article and Find Full Text PDFPalladium-Catalyzed Alkoxycarbonylation of Alcohols for the Synthesis of Cyclobutanecarboxylates with α-Quaternary Carbon Centers.
Org Lett
January 2025
Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany.
A palladium-catalyzed alkoxycarbonylation with two different alcohols for the synthesis of cyclobutanecarboxylates bearing an α-quaternary carbon center is presented. The reaction utilizes readily accessible starting materials, tolerates a broad scope of functional groups, and provides a straightforward and efficient approach for the synthesis of a diverse array of cyclobutanecarboxylates bearing an α-quaternary carbon. Meanwhile, this strategy effectively prevents the transition-metal-catalyzed ring-opening of cyclobutanols, preserves the cyclobutane framework, and affords 1,1-disubstituted cyclobutanecarboxylates in high yields with excellent regioisomeric ratios.
View Article and Find Full Text PDFPalladium-Catalyzed Oxidative Allene-Allene Cross-Coupling.
J Am Chem Soc
January 2025
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.
Direct cross-coupling reactions between two similar unactivated partners are challenging but constitute a powerful strategy for the creation of new carbon-carbon bonds in organic synthesis. [4]Dendralenes are a class of acyclic branched conjugated oligoenes with great synthetic potential for the rapid generation of structural complexity, yet the chemistry of [4]dendralenes remains an unexplored field due to their limited accessibility. Herein, we report a highly selective palladium-catalyzed oxidative cross-coupling of two allenes with the presence of a directing olefin in one of the allenes, enabling the facile synthesis of a broad range of functionalized [4]dendralenes in a convergent modular manner.
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