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Catalytic System-Controlled Regioselective 1,2- and 1,4-Carboannulations of [60]Fullerene.
Org Lett
April 2024
Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Selective functionalization of fullerenes is an important but challenging topic in fullerene chemistry and synthetic chemistry. Here we present the first example of catalytic system-controlled regioselective 1,2- and 1,4-addition reactions for the flexible and efficient synthesis of novel 1,2- and 1,4-carbocycle-fused fullerenes via a palladium-catalyzed decarboxylative carboannulation process.
View Article and Find Full Text PDFElectronically flexible PYA ligands for efficient palladium-catalyzed α-arylation of ketones.
Dalton Trans
November 2023
Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
Palladium-catalyzed cross-coupling chemistry and in particular ketone α-arylation has been relying on a rather narrow range of supporting ligands with almost no alternatives to phosphines and N-heterocyclic carbenes. Here we introduce a class of well-defined palladium(II) complexes supported by ,'-chelating and electronically flexible pyridylidene amide (PYA)-pyridyl ligands as catalysts for efficient α-arylation of ketones. Steric and electronic variations of the ,'-bidentate ligand indicate that the introduction of an -methyl group on the pyridinum heterocycle of the PYA ligand enhances the arylation rate and prevents catalyst deactivation, reaching turnover numbers up to 7300 and turnover frequencies of almost 10 000 h, which is similar to that of the best phosphine complexes known to date.
View Article and Find Full Text PDFFlexible Axial Shielding Strategy for Improving Ethylene (Co)polymerization with 8-Cycloalkylnaphthyl α-Diimine Catalysts.
Inorg Chem
September 2023
Anhui Laboratory of Molecule-Based Materials, Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China.
8-aryl or alkyl-naphthyl substituents are widely used as an effective axial shielding strategy for the suppression of chain transfer in late-transition metal-catalyzed ethylene (co)polymerization to yield high molecular weight polyethylene and copolymers. In this study, two 8-cycloalkylnaphthyl acenaphthene-based α-diimine ligands and the corresponding four nickel and palladium complexes were designed and synthesized to explore the effect of axial flexible shielding on ethylene (co)polymerization. In ethylene polymerization, the nickel complexes displayed high activities (up to 1.
View Article and Find Full Text PDFSynthesis of β-Deuterated Amino Acids via Palladium-Catalyzed H/D Exchange.
J Org Chem
December 2022
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergistic Innovation Center for Advanced Materials (SICAM), Nanjing Tech. University (Nanjing Tech.), 30 Puzhu Road, Nanjing 211816, P. R. China.
Despite several synthetic approaches that have been developed for α-deuterated amino acids, the synthesis of β-deuterated amino acids has remained a challenge. Herein, we disclose a palladium catalyzed H/D exchange protocol for a β-deuterated N-protected amino amide, which can be converted to a β-deuterated amino acid simply by removal of protecting groups. This protocol is highly efficient, simply manipulated, and appliable for deuterium-labeling of many amino amides.
View Article and Find Full Text PDFHoogsteen triplexes stabilized through ethynyl-linked pyrene-indole synthesized by high-temperature Sonogashira coupling.
Org Biomol Chem
November 2022
Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, DK-5230, Odense M, Denmark.
The low binding affinity of unmodified triplex-forming oligonucleotides (TFO) is the main drawback to their promising utilization in gene therapy. In the present study, we have synthesized DNA intercalator 5-(pyren-1-ylethynyl)indole Y, known as twisted intercalating nucleic acid (TINA), by a Cu-mediated Sonogashira palladium-catalyzed coupling reaction of 1-ethynylpyrene with 5-iodoindole at a high temperature under anaerobic conditions. Coupling with indole C-5 was far more preferable in obtaining stable TINA-indole than enamine site C-3, as neither hydration of the triple bond to ketones nor competitive Glaser-type homocoupling of acetylenes was observed.
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