An unprecedented Lewis acid-catalyzed cascade 1,3-rearrangement/Friedel-Crafts cyclization of propargyl acetates is developed for the construction of polycyclic bridged indene derivatives in moderate to good yields. This practical procedure features mild conditions, broad substrate scope, and easy operation.
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http://dx.doi.org/10.1039/c9cc03715b | DOI Listing |
Acc Chem Res
January 2025
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.
View Article and Find Full Text PDFChem Asian J
January 2025
Xiamen University, Department of Chemistry, Xiamen University, Lujiaxi Building Room 742, 361005, xiamen, CHINA.
The direct construction of polycyclic arenes through ring formation using simple building blocks is highly appealing but remains challenging in organic chemistry. In this study, we introduce an efficient cascade reaction that combines dearomatizing photocyclization with oxidative aromatization, driven by organophotocatalysis. Conducted under mild, transition-metal-free conditions, this reaction seamlessly converts styrene derivatives into a diverse array of functionalized polycyclic aromatic compounds with good yields and regioselectivity.
View Article and Find Full Text PDFOrg Lett
January 2025
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 211800, China.
A palladium-catalyzed tandem reaction of 1-(2-iodophenyl)-3-arylprop-2-yn-1-ones and 1-(2-azidophenyl)propargyl ethers is developed to provide the rapid construction of a fused polycyclic indenone-indole scaffold under mild conditions. The reaction proceeds via a highly ordered process involving Sonogashira coupling, propargyl-allenyl isomerization, allene-azide cycloaddition, denitrogenation, and diradical coupling. The proposed reaction mechanism is supported by experimental and computational studies.
View Article and Find Full Text PDFACS Appl Mater Interfaces
January 2025
College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, No. 30, South Puzhu Road, Nanjing 211816, China.
Due to the low bioavailability and insolubility of high molecular weight polycyclic aromatic hydrocarbons (HMW-PAHs) in aqueous solutions, their degradation efficiency is significantly limited in wastewater treatment and environmental remediation. To address this challenge, we designed oil-in-water (O/W) macroemulsion (ME) bioreactors with mixed surfactants (Tween-80 and Triton X-100), -butanol, corn oil, and () to enhance the degradation efficiency of pyrene. Owing to the higher solubility of pyrene in MEs, it could be easily adsorbed onto hydrophobic groups on the cell surface.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin, 300071, P. R. China.
Reliable methods for rapidly constructing C(sp)-rich three-dimensional polycycles are in high demand for organic synthesis and medicinal chemistry. Although there are various mature systems for synthesizing five- or six-membered polycycles, a catalytic platform for accessing diverse cycloheptanoid-containing polycyclic scaffolds is lacking. Herein, we describe a method for copper-catalyzed intramolecular 2-aminoallyl cation-diene (4+3) cycloaddition reactions.
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