Iron(salan) complex 1 was found to catalyze the oxidative dearomatization of 1-substituted 2-naphthols with the formation of an all-carbon quaternary stereocenter in air in the presence of nitroalkanes, to afford the corresponding cyclic enones with high enantioselectivity of 88-96% ee.
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http://dx.doi.org/10.1021/ja310203c | DOI Listing |
Chem 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 PDFJ Hazard Mater
January 2025
School of Environmental Science and Engineering, Southwest Jiaotong University, Sichuan, Chengdu 611756, China. Electronic address:
The ultraviolet-activated peroxymosnofulate (UV/PMS) system, an effective advanced oxidation process for removing dissolved organic matter (DOM) from wastewater, is limited by high chloride ion (Cl) concentrations in landfill leachate. This study used Fourier transform ion cyclotron resonance mass spectrometry to explore the transformation of DOM in the UV/PMS system with a high Cl concentration. The results revealed that elevated Cl levels generate reactive chlorine species, including chlorine radicals, dichlorine radicals, and hypochlorous acid/hypochlorite, reducing the total organic carbon (TOC) removal efficiency of Suwannee River natural organic matter (SRNOM) from 78.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States.
We present the serendipitous discovery of an unusual dimer formed from anthracene-derived polyarenes. Unlike the typical oxidative coupling of substituted aromatic scaffolds, the reaction yielded a dearomatized enone dimer as the sole product. This dearomatized motif, notably, does not undergo the commonly observed rearomatization, and no biaryl products were detected.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
An electrochemical method for the oxidative dearomatization of electron-deficient phenols by employing tetrabutylammonium bromide as a mediator under aqueous biphasic conditions is reported. This approach represents a safer alternative to the use of stoichiometric chemical oxidants and enables oxidative dearomative spirolactonization and spiroetherification reactions. Compared to previous approaches based on direct electrolysis, this strategy expands the substrate scope to electron-deficient phenols.
View Article and Find Full Text PDFChem Sci
November 2024
Molecular Inorganic Chemistry and Catalysis, Inorganic and Structural Chemistry, Center for Molecular Materials, Faculty of Chemistry, Universität Bielefeld Universitätsstrasse 25 D-33615 Bielefeld Germany http://www.ghadwalgroup.de.
The first carbocyclic gallylene [(ADC)Ga(GaI)] and bis-gallylene [(ADC)Ga] (ADC = PhC{N(Dipp)C}; Dipp = 2,6-iPrCH) featuring a central CGa ring annulated between two 1,3-imidazole rings are prepared by KC reductions of [(ADC)GaI]. Treatment of [(ADC)Ga] with Fe(CO) affords complex [(ADC)GaFe(CO)] in which each Ga(i) atom serves as a two-electron donor. [(ADC)Ga] activates white phosphorus (P) and the C -F bond of aryl fluorides (ArF) to yield compounds [(ADC)Ga(P)] and -/-[(ADC)GaF(Ar)], respectively.
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