Herein we describe a Cu-catalyzed radical addition and oxidation cascade reaction for the chemo/regioselective synthesis of unsymmetrical indole trimers (isotriazatruxenes, -TATs) from easily available starting materials. The -TATs exhibited blue fluorescence in various solvents with different fluorescence intensities and showed good structural expansibility. A wider range of products could be used in optoelectronic materials by developing suitable derivatives.
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http://dx.doi.org/10.1021/acs.orglett.2c00180 | DOI Listing |
Angew Chem Int Ed Engl
November 2024
Department of Chemistry, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, Pennsylvania, 15213, United States.
Photomediated Atom Transfer Radical Polymerization (photoATRP) is an activator regeneration method, which allows for the controlled synthesis of well-defined polymers via light irradiation. Traditional photoATRP is often limited by the need for high-energy ultraviolet or violet light. These could negatively affect the control and selectivity of the polymerization, promote side reactions, and may not be applicable to biologically relevant systems.
View Article and Find Full Text PDFJ Am Chem Soc
November 2024
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
The direct use of readily available aldehydes as acyl radical precursors has facilitated diverse three-component acylative difunctionalization reactions of alkenes, offering a powerful route to synthesize β-branched ketones. However, asymmetric three-component acylative difunctionalization of alkenes with aldehydes still remains elusive. Here we report a copper-catalyzed asymmetric three-component radical acylarylation of vinylarenes with aldehydes and aryl boronic acids.
View Article and Find Full Text PDFOrg Lett
November 2024
Department of Chemistry, Kwangwoon University, Seoul 01897, Republic of Korea.
A copper-catalyzed hydrodechlorination of primary, secondary, and tertiary alkyl chlorides using diisobutylaluminum hydride is reported. This catalytic system offers a broad substrate scope, high yields, and good functional group tolerance. Mechanistic investigations indicated that the reaction predominantly proceeds via a radical pathway, as supported by radical clock experiments.
View Article and Find Full Text PDFJ Am Chem Soc
November 2024
Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221, United States.
Cu-catalyzed enantioconvergent cross-coupling of alkyl halides has emerged as a powerful strategy for synthesizing enantioenriched molecules. However, this approach is intrinsically limited by the weak reducing power of copper(I) species, which restricts the scope of compatible nucleophiles and necessitates extensive ligand optimization or the use of complex chiral scaffolds. To overcome these challenges, we introduce an aryl-radical-enabled strategy that decouples the alkyl halide activation step from the chiral Cu center.
View Article and Find Full Text PDFChemistry
December 2024
Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Pingyuan Laboratory and College of Chemistry, Zhengzhou University, 75 Daxue Road North, Zhengzhou, 450052, China.
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