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Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, a photochemical radical cyclization reaction of -vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as aryl radical precursors at room temperature. This approach allowed good functional group tolerance and substrate applicability.
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http://dx.doi.org/10.1021/acs.joc.4c03121 | DOI Listing |
J Mol Model
September 2025
School of Mechanical Engineering and Automation, Fuzhou University, Fuzhou, 350116, People's Republic of China.
Context: This study systematically investigates the growth mechanism of nitrogen-doped graphene in a plasma environment, with a particular focus on the effects of temperature and hydrogen radicals on its structural evolution. The results reveal that, at 3000 K, the formation of nitrogen-doped graphene proceeds through three stages: carbon chain elongation, cyclization, and subsequent condensation into planar structures. During this process, nitrogen atoms are gradually incorporated into the carbon network, forming various doping configurations such as pyridinic-N, pyrrolic-N, and graphitic-N.
View Article and Find Full Text PDFOrg Lett
September 2025
Precise Synthesis and Function Development Key Laboratory of Sichuan Province, China West Normal University, Nanchong, 637002, China.
A novel strategy for accessing unprecedented silyl/fluoroalkyl-embedded tetracyclic pyrrolizidinediones has been developed through the visible-light-induced cascade cyclization of 3-methyleneisoindolin-1-ones using hydrosilanes or fluoroalkylsulfinate salts as radical sources under redox-neutral conditions. This protocol features mild reaction conditions, operational simplicity, and excellent compatibility with various functional groups. A number of silyl/fluoromethyl-decorated tetracyclic pyrrolizidinedione frameworks were efficiently created.
View Article and Find Full Text PDFJ Org Chem
September 2025
New Materials and Green Manufacturing Talent Introduction and Innovation Demonstration Base, School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan, China 430068.
A copper-catalyzed denitrogenative radical cyclization of 3-aminoindazoles with -cyanoarylacrylamides has been developed, enabling the efficient synthesis of a variety of cyanoarylated quinoline-2,4(1,3)-diones in moderate to good yields at room temperature. Notably, this strategy overcomes the traditional challenge of the low reactivity of nitrile groups toward radical addition by utilizing cyanoaryl radicals generated from 3-aminoindazoles as reactive intermediates. Mechanism studies indicate that 2-cyanophenyl radicals, generated through the cleavage of two C-N bonds of 3-aminoindazoles, served as the key intermediates initiating the cyclization process.
View Article and Find Full Text PDFJ Org Chem
September 2025
Yunnan Key Laboratory of Modern Separation Analysis and Substance Transformation, College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, Yunnan Province 650500, P. R. China.
Photoinduced trifluoroethyl and acyl radical procedures for the efficient and simple preparation of iodotrifluoroethylated and acylated pyrrolidine-2-ones from -tethered 1,6-enynes with 1,1,1-trifluoro-2-iodoethane and acyl oxime esters are reported. The photoinduced iodotrifluoroethylation is performed via the energy transfer (EnT) process of the fluorescein sodium-mediated atom-transfer radical addition (ATRA) strategy under visible-light irradiation. The acylation is carried out with 4CzIPN as an organophotocatalyst at room temperature under metal- and oxidant-free conditions.
View Article and Find Full Text PDFOrg Lett
September 2025
Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079
Structurally diverse 1,2-sulfinate-sulfonate esters are shown to be conveniently prepared through visible light-induced sulfonation and sulfinylation of difunctionalized alkenes using alcohols and NaHSO. The reactions proceed under mild conditions in the presence of photocatalysts and HCOH as an additive, exhibiting good functional group tolerance and a broad scope. Furthermore, this method is scalable and has been successfully applied to synthesize 1,2-disulfonic acid esters.
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