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Selective and Divergent Synthesis of Naphthalene- and Phenanthrene-Fused Azahelicenes by Turning Rearrangement On or Off.
Chemistry
January 2025
Okayama Daigaku Daigakuin Shizen Kagaku Kenkyuka, Division of Applied Chemistry, JAPAN.
The Scholl reaction has been used to synthesize a variety of polycyclic aromatic hydrocarbons, where 1,2-aryl shifts have sometimes occurred to yield unique rearrangement products. However, such 1,2-aryl shifts are often uncontrollable, and the selective and divergent synthesis with or without rearrangement is desired. Here, we achieved the control of the rearrangement in the Scholl reaction of carbazoles by the N-substituents.
View Article and Find Full Text PDFPalladium-Catalyzed Tandem Reactions via Allene Intermediates for the Rapid Synthesis of a Fused Indenone-Indole Scaffold.
Org 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 PDFVolatile Organic Compounds Inside Homes Impacted by Smoke from the Marshall Fire.
ACS EST Air
January 2025
Department of Chemistry, University of Colorado Boulder, Boulder, Colorado 80309, United States.
Wildfires at the wildland-urban interface (WUI) have been increasing in frequency over recent decades due to increased human development and shifting climatic patterns. The work presented here focuses on the impacts of a WUI fire on indoor air using field measurements of volatile organic compounds (VOCs) by Proton-Transfer-Reaction Time-of-Flight Mass Spectrometry (PTR-TOF-MS). We found a slow decrease in VOC mixing ratios over the course of roughly 5 weeks starting 10 days after the fire, and those levels decreased to ∼20% of the initial indoor value on average.
View Article and Find Full Text PDFBuilding Three-Dimensional Complexity by Intramolecular 2-Aminoallyl Cation-Diene (4 + 3) Cycloaddition.
Angew Chem Int Ed Engl
January 2025
Nankai University, College of Chemistry, 94 Weijin Rd., 300071, Tianjin, CHINA.
Reliable methods for rapidly constructing C(sp3)-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.
View Article and Find Full Text PDFKey role of persistent free radicals in soil for persulfate activation: impacts on benzo[]pyrene degradation.
Environ Sci Process Impacts
January 2025
Key Laboratory of Industrial Ecology and Environmental Engineering (Ministry of Education), School of Environmental Science and Technology, Dalian University of Technology, Dalian, 116024, China.
Environmentally persistent free radicals (EPFRs) have been widely detected in polycyclic aromatic hydrocarbon (PAH)-contaminated soils, but the activation of persulfate by inherent EPFRs in PAH-contaminated soil for the transformation of PAHs remains unclear. In the present study, benzo[]pyrene (B[]P) was selected as a representative PAH and its transformation in a persulfate/B[]P-contaminated soil system was studied without the addition of any other activator. Results indicated that EPFRs in the soil activated persulfate to produce reactive oxygen species (ROS) and degraded B[]P.
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