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Herein, we describe the direct synthesis of pyrrolo[1,2-α]quinoxaline oxidative coupling between methyl arene and 1-(2-aminophenyl) pyrroles. Oxidation of the benzylic carbon of the methyl arene was achieved by di--butyl peroxide in the presence of an iron catalyst, followed by conversion to an activated aldehyde . Oxygen played a crucial role in the oxidation process to accelerate benzaldehyde formation. Subsequent Pictet-Spengler-type annulation completed the quinoxaline structure. The protocol tolerated various kinds of functional groups and provided 22 4-aryl pyrrolo[1,2-α]quinoxalines when various methyl arene derivatives were used. The developed method proceeded in air, and all catalysts, reagents, and solvents were easily accessible.
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http://dx.doi.org/10.1021/acs.joc.1c00371 | DOI Listing |
Org Lett
August 2025
Academy of Chinese Medical Science, Henan University of Chinese Medicine, Zhengzhou 450046, China.
Carboranes, serving as three-dimensional surrogates for benzene and core skeletons of boron neutron capture therapy (BNCT) reagents, have become increasingly vital in medicinal chemistry. Traditional carbon-site functionalization of carboranes relying on strong base-mediated deprotonation inherently restricts reaction diversity. Herein, we report a polarity-matching-driven halogen atom transfer strategy, enabling the generation of open-shell carbon-centered carborane radicals.
View Article and Find Full Text PDFJ Am Chem Soc
August 2025
Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, D-14476 Potsdam, Germany.
Micellar catalysis offers a sustainable and effective alternative to traditional systems. This study introduces a micellar platform based on the amphiphilic diblock copolypeptoid poly(-methyl glycine)--poly(-n-propyl glycine) for direct arene cyanation in water. The polymer was used to encapsulate the photoredox catalyst 3,6-di--butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (Mes-Acr-Ph), forming core-shell nanostructures, as confirmed by dynamic light scattering (DLS) and cryogenic transmission electron microscopy (cryo-TEM).
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July 2025
Synthèse Organométallique et Catalyse, UMR-CNRS 7177 Institut de Chimie de Strasbourg, Strasbourg University, 67008 Strasbourg, France.
The cationic chloro--{[4-(diphenylphosphanyl)phenyl]-,-dimethylmethanammonio(norbornadiene)rhodium(I) complex was encapsulated inside a self-assembled hexameric capsule. This capsule was obtained through a reaction involving 2,8,14,20-tetra-undecyl-resorcin[4]arene and water in chloroform. The formation of an inclusion complex was deduced from a combination of spectral measurements (UV-visible spectroscopy, H, P{H} NMR and DOSY).
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July 2025
Laboratory of Inorganic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece.
Searching for new and efficient transfer hydrogenation catalysts, a series of new organometallic ruthenium(II)-arene complexes of the formulae [Ru(η--cymene)(L)Cl][PF] (-) and [Ru(η--cymene)(L)Cl][Ru(η--cymene)Cl] (-) were synthesized and fully characterized. These were prepared from the reaction of pyridine-quinoline and biquinoline-based ligands (L) with [Ru(η--cymene)(μ-Cl)Cl], in 1:2 and 1:1, metal (M) to ligand (L) molar ratios. Characterization includes a combination of spectroscopic methods (FT-IR, UV-Vis, multi nuclear NMR), elemental analysis and single-crystal X-ray crystallography.
View Article and Find Full Text PDFJ Am Chem Soc
August 2025
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, United States.
The tungsten fragment {WTp(NO)(PMe)} (Tp = trispyrazolylborate) is an effective dearomatization agent for benzene and its derivatives. The dihapto-coordination of this system to an arene disrupts its aromatic stability, thereby promoting facile electrophilic additions to the hydrocarbon, which can then be followed by the addition of nucleophiles. This preliminary study endeavors to extend this conceptual approach to other aromatic and antiaromatic carbocycles.
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