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Over the past decade, significant progress has been made in the direct C-H acylation of naphthalenes, occurring at the α or β-positions to yield valuable ketones through Friedel-Crafts acylation or transition-metal-catalysed carbonylative coupling reactions. Nevertheless, highly regioselective acylation of naphthalenes remains a formidable challenge. Herein, we developed a nickel-catalysed reductive ring-opening reaction of 7-oxabenzonorbornadienes with acyl chlorides as the electrophilic coupling partner, providing a new method for the exclusive preparation of β-acyl naphthalenes.
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http://dx.doi.org/10.1039/d4cc01660b | DOI Listing |
Org Lett
September 2025
School of Chemistry and Chemical Engineering, Hefei University of Technology and Anhui Province Key Laboratory of Value-Added Catalytic Conversion and Reaction Engineering, Hefei 230009, China.
Under visible-light photocatalysis facilitated by cobalt coordination, a highly regio- and stereoselective cycloisomerization reaction of 1,6-enynes has been developed. This method enables the efficient synthesis of various skipped 1,4-diene products with excellent stereoselectivity, using commercially available cobalt catalysts, ligands, and reagents. Notably, the reaction exhibits remarkable regioselectivity (>20:1), stereoselectivity (/ > 20:1), and high yields (58-92%) under mild conditions, along with a broad substrate scope and good functional group tolerance.
View Article and Find Full Text PDFJ Org Chem
September 2025
National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650500, P. R. China.
We herein describe a novel decarboxylation/cyclization sequence involving a three-component reaction of dialkyl 2-(alkoxymethylene)malonate, amines, and terminal alkyne ester or internal alkyne ester catalyzed by CsCO under microwave conditions. These two types of highly chemo- and regioselective transformations were accomplished by different reaction channels to furnish a wide range of functionalized 8-hydroxyisoquinoline-1(2)-ones (21 examples) and 2-pyridones (18 examples) in good to excellent yields and might provide new opportunities for the discovery of N-heterocyclic drugs and other functional molecules.
View Article and Find Full Text PDFNat Commun
September 2025
Department of Chemistry, Institute of Silicon Chemistry and Catalysis Research Center, TUM School of Natural Sciences, Technische Universität München, Garching bei München, Germany.
Catalytic reduction of quinolines has gained continuous interest in both academia and industry, providing direct and efficient access to tetrahydroquinolines or 1,2-dihydroquinolines. The catalytic preparation of tetrahydroquinolines has been extensively studied by transition metal complexes. By contrast, the related catalytic synthesis of 1,2-dihydroquinolines remains underdeveloped due to the difficulties in achieving precise control over both chemo- and regioselectivity.
View Article and Find Full Text PDFChem Sci
August 2025
College of Chemistry and Chemical Engineering, Jiangxi Province Engineering Research Center of Ecological Chemical Industry, Jiujiang University Jiujiang 332005 China
BN-fused aromatic compounds have garnered significant attention due to their unique electronic structures and exceptional photophysical properties, positioning them as highly promising candidates for applications in organic optoelectronics. However, the regioselective synthesis of BN isomers remains a formidable challenge, primarily stemming from the difficulty in precisely controlling reaction sites, limiting structural diversity and property tunability. Herein, we propose a regioselective synthetic strategy that employs 2,1-BN-naphthalene derivatives, wherein selective activation of N-H and C-H bonds is achieved in conjunction with -halogenated phenylboronic acids.
View Article and Find Full Text PDFBiochimie
September 2025
Univ. Bordeaux, CNRS, LBM, UMR 5200, Villenave d'Ornon, F-33140 France. Electronic address:
Marine microalgae are the primary producers of important lipids in oceanic ecosystems. In particular, they sustain the food web with omega-3 very-long-chain polyunsaturated fatty acids (n-3 PUFAs), which play a protective role against various human metabolic disorders and are thus considered highly beneficial to health. Ostreococcus tauri is a marine pico-eukaryote that contains high levels of several n-3 PUFAs, including docosahexaenoic acid (22:6n3; DHA), octadecapentaenoic acid (18:5n3, OPA), and hexadecatetraenoic acid (16:4n3), each with a distinct distribution.
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