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A silver-catalyzed cascade cyclization reaction of isocyanides with sulfoxonium ylides has been developed for the first time. This reaction provides a new and efficient method for the construction of highly functionalized 3-aminofurans and 4-aminoquinolines from readily available starting materials in a single step.
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http://dx.doi.org/10.1021/acs.orglett.0c02835 | DOI Listing |
J Am Chem Soc
June 2025
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, California Institute of Technology, MC-101-20, Pasadena, California 91125, United States.
We disclose the first total syntheses of the complex alkaloids Lycojapomine A and B. Our synthetic strategy is built on a dearomatization and stepwise functionalization of a pyrrole starting material, constructing the three-dimensional structure of the target around it. This is enabled by a high-yielding photoinduced primary radical addition from the -hydroxy phthalimide ester and a subsequent silver-catalyzed 5-endo-dig and Aza-silyl-Prins annulation cascade.
View Article and Find Full Text PDFOrg Lett
June 2025
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding 071002, China.
The enantioselective synthesis of carbazoles and pyrroloindolines has been achieved through organo-catalyzed and metal sequential-catalyzed one-pot reactions of indolyl ynones. Chiral carbazoles can be synthesized from the reactions of indolyl ynones and nitroolefins through an organo-catalyzed Michael addition followed by a gold-catalyzed Friedel-Crafts reaction/aromatization process. The reactions of indolyl ynones and N-tosyl imines lead to the generation of pyrroloindolines via an organo-catalyzed Mannich reaction and a silver-catalyzed dearomatizing spirocyclization/N,N-acetalization cascade reaction.
View Article and Find Full Text PDFACS Omega
April 2025
Peptide Chemistry Research Institute, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran.
We describe a novel approach for synthesizing diverse fused heterocyclic compounds by utilizing a sequential silver(I) catalyzed reaction between readily obtainable -amidonaphthyridin ylide and dialkyl acetylenedicarboxylates. This method provides an efficient approach for the selective synthesis of tetracyclic ring-fused 1,6-naphthyridine and isoquinoline derivatives, offering exceptional structural diversity. In addition, the title compounds constitute an interesting class of luminophores with tunable emission solvatochromicity.
View Article and Find Full Text PDFOrg Lett
May 2025
State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
Direct construction of the piperazine scaffolds with multiple functionalities remains important yet challenging. Herein, a silver-catalyzed formal [3 + 3] heteroannulation of aziridines with 3-aminoacrylates via ring-opening and vinyl C(sp)-H amination for the direct synthesis of tetrasubstituted 1,4,5,6-tetrahydropyrazines is reported. Upon the catalytic activation of the silver Lewis acid, this protocol enables the formation of two new C-N bonds through selective nucleophilic ring-opening and C-H aminative cyclization cascades, featuring a broad substrate scope and a good functional group tolerance with excellent selectivity.
View Article and Find Full Text PDFJ Org Chem
January 2025
Faculty of Science, Kunming University of Science and Technology, Jingming South Road 727, Chenggong District, Kunming 650500, P. R. China.
A novel silver-catalyzed cascade radical isonitrile insertion and defluorinative cyclization have been developed to synthesize CFH- and phosphinoyl-containing quinolines from -isocyanyl α-trifluoromethylstyrenes. The reaction proceeded under redox-neutral conditions and allowed the construction of a highly attractive quinoline ring system, with the simultaneous formation of the CFH group and introduction of various phosphinoyl groups in a single transformation, showing operational simplicity, a wide substrate scope, good tolerance for functional groups, and remarkable atom-/stepeconomy. Mechanistic studies indicated that the reaction is likely to involve the participation of P-centered radicals and key carbanion intermediates.
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