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The oxidative coupling between two carbon-hydrogen (C-H) bonds offers the most straightforward pathway to construct C-C bonds from hydrocarbons without pre-functionalization, exhibiting high step- and atom-economy. This article features the recent advances in the oxidative coupling of unactivated Csp-H with different hybrid C-H bonds, including Csp-H, Csp-H and Csp-H bonds. The substrate scope, proposed mechanism and application of these reactions are summarized, intending to provide insights toward developing novel and efficient protocols for Csp-C bond construction.
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http://dx.doi.org/10.1039/d1cc04802c | DOI Listing |
Proc Biol Sci
September 2025
Department of Biology, Evolutionary Ecology and Infection Biology, Lund University, SE-223 62, Lund, Sweden.
Incubation temperature affects both growth and energy metabolism in birds after hatching. Changes in cellular mechanisms, including mitochondrial function, are a likely but unexplored explanation for these effects. To test whether temperature-dependent changes to mitochondria may link embryonic development to the post-natal phenotype, we incubated Japanese quail eggs at constant low (36.
View Article and Find Full Text PDFJ Org Chem
September 2025
State Key Laboratory of Chemical Resource Engineering, Institute of Computational Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.
The -di(2-pyridyl)arenes, featuring a unique structure, hold significant promise for applications in fluorescent probes, synthetic nanoparticle stabilizers, and chemical synthesis. The mechanism of Ru-catalyzed decarboxylation and heteroarylation reactions of aryl carboxylic acids to access -dipyridylarenes was elucidated using DFT calculations, which involved C-H bond activation, oxidative addition, reductive elimination, and decarboxylation processes to form -di(2-pyridyl)arenes. The rate-determining step of the reaction is the second reductive elimination step with an energy barrier of 27.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2025
Shenzhen Grubbs Institute, Department of Chemistry, Guangming Advanced Research Institute, and Shenzhen Key Laboratory of Cross-Coupling Reactions, Southern University of Science and Technology, Shenzhen, 518055, China.
Despite the widespread utility of transition metal-catalyzed cross-couplings in organic synthesis, the coupling of unactivated alkyl electrophiles remains challenging due to sluggish oxidative addition and competing side reactions. Here, we describe a general and practical copper-catalyzed radical deoxyalkynylation of α-unfunctionalized alcohols through a synergistic combination of Barton-McCombie deoxygenation and copper-catalyzed radical cross-coupling. Key to the success of this method lies in not only the development of rigid anionic multiple N,N,N-ligand to exert remarkable selectivity of highly reactive unactivated alkyl radicals, but also the selection of one suitable oxidant to suppress Glaser homocoupling and other side products.
View Article and Find Full Text PDFJ Am Chem Soc
September 2025
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19014, United States.
Phenol overoxidation has severely hindered the advancement and synthetic utility of oxidative phenol coupling for over two decades, preventing the development of general catalytic methods. Electron-deficient phenols resist selective coupling due to their high oxidation potential, while monosubstituted phenols undergo uncontrolled overoxidation, making their selective transformation highly challenging. We present a strategy that harnesses biphenol-boron complexation to suppress overoxidation, unlocking the selective catalytic oxidative coupling of both electron-deficient and monosubstituted phenols.
View Article and Find Full Text PDFJ Agric Food Chem
September 2025
Institute of Agriculture, Tokyo University of Agriculture and Technology, Tokyo 183-8509, Japan.
The -hydroxyphenyl (H) unit is an aromatic structure found in lignin, particularly abundant in compression wood and grass, and is derived from the incorporation of -coumaryl alcohol (-CMA). Although the structural and biosynthetic aspects of lignin have been extensively studied, the polymerization reactivity of H-unit during lignification remains poorly understood. In this study, horseradish peroxidase (HRP)-catalyzed homo- and co-oxidative coupling reactions (initial stage of enzymatic dehydrogenative polymerization) with -CMA and/or coniferyl alcohol (CA) were performed to investigate monolignol consumption, dilignol formation, and their potential involvement in subsequent polymerization.
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