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A novel and efficient strategy for the synthesis of sterically hindered 4-amino-3-acyl-2-naphthols through a palladium-catalyzed coupling reaction involving isocyanide chemselective insertion and domino isomerization has been developed. The methodology, which is in accordance with the principle of "atom and step economy", efficiently constructs 4-amino-3-acyl-2-naphthols in moderate to good yields.
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http://dx.doi.org/10.1021/acs.joc.5b01269 | DOI Listing |
Org 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%.
View Article and Find Full Text PDFOrg Lett
July 2025
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
Herein, we present an enantioselective domino carboetherification of β,γ-unsaturated oxime derivatives under mild reaction conditions. This process, catalyzed by palladium in combination with Sadphos ligands, offers a concise and highly efficient route for the assembly of chiral isoxazoline-linked methylenedihydrobenzofuran and methyleneindolin bis-heterocyclic scaffolds. The methodology demonstrates excellent functional group tolerance, a broad substrate scope, and high chemoselectivity and enantioselectivity.
View Article and Find Full Text PDFOrg Lett
April 2025
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
A palladium-catalyzed reaction of indoles with cyanoacetate salts enables the synthesis of 2,6-disubstituted indolines via tandem dearomatization/decarboxylative cyanomethylation. Remarkably, this is the first example of indole difunctionalization at the C2 and C6 positions. Moreover, this methodology extends to the palladium-catalyzed cyclization/decarboxylative cyanomethylation of aryl halide-tethered alkenes.
View Article and Find Full Text PDFChem Commun (Camb)
April 2025
College of Chemistry and Chemical Engineering, Nantong University, Nantong, 226019, P. R. China.
Until now, the σ-alkylpalladium species in C-H alkylation of polyfluoroarenes were largely limited to palladium-catalyzed domino intramolecular cyclization of -iodophenol-derived allyl ethers or -aryl acrylamides. Herein, we disclose a sequential three-component intermolecular carbopalladation/Heck cyclization/intermolecular C-H bond functionalization of -iodostyrenes, polyfluoroarenes, internal alkynes or oxanorbornadiene (ONBD), thus assembling various alkylated polyfluoroarene derivatives containing an indene skeleton. Additionally, dialkylated polyfluoroarenes containing two indenes can be constructed by the dual reaction strategy.
View Article and Find Full Text PDFOrg Biomol Chem
April 2025
Hubei Key Laboratory of Nanomedicine for Neurodegenerative Diseases, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China.
Herein, a palladium-catalyzed cross-coupling cascade cyclization of alkene-tethered indoles and ()-β-chlorovinyl ketones, providing access to various furan-bearing indolo[2,1-]isoquinolines, is reported. The reaction enables the rapid construction of one C-O bond and two C-C bonds to form bis-heterocycles. Furthermore, these furan-bearing indolo[2,1-]isoquinolines exhibited certain antifungal activity .
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