The efficient palladium-catalyzed synthesis of a range of substituted 2H-Indazoles via C-H arylation is reported. Reactions are performed on water and provide a direct and mild route toward 2,3-diaryl indazoles of widespread biological significance.
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http://dx.doi.org/10.1021/ol902537d | DOI Listing |
Chem
October 2024
Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Arylethylamines represent a privileged scaffold in pharmaceutical compounds and form the backbone of many medical drugs, including those used for treating neurological diseases and pain. Their biomedical significance has inspired new synthetic methods that rely on transition metal-catalyzed aminoarylation reaction to an alkene, often in conjunction with a photoredox catalyst or a photosensitizer, and guided by a directing or stabilizing group. Here, we introduce a simple and effective method for azidoarylation of unactivated alkenes under transition metal-free conditions.
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December 2024
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China.
Functionalized polycyclic aromatic hydrocarbons (PAHs) are essential building blocks for the bottom-up fabrication of structurally uniform nanocarbons. Herein we report a simple and efficient synthetic method toward K-region hydroxy-functionalized PAHs via TEMPO-mediated twofold intramolecular C-H/C-H arylations of 1-biphenyl-2-yl-2-aryl-ethanone derivatives. This method achieves high yields and selectivity, synthesizing a variety of PAH frameworks, including pyrenes, chrysenes, benzo[]phenanthrenes, and benzo[]tetraphenes.
View Article and Find Full Text PDFOrg Lett
December 2024
Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India.
Remote C4-H functionalization of -naphthoic acids is highly challenging due to the presence of proximally more accessible C-H bonds at the C2 and C8 positions. Herein, we report the first palladium-catalyzed direct C4 arylation of 1-naphthamides with high regioselectivity and excellent functional group compatibility. Diverse aryl couples were found to be compatible with C4 arylation.
View Article and Find Full Text PDFMacromol Rapid Commun
November 2024
School of Materials Science and Engineering, Tianjin Key Laboratory of Molecular Optoelectronic Science and Key Laboratory of Organic Integrated Circuits, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Ministry of Education, Tianjin University, Tianjin, 300072, P. R. China.
Chemistry
November 2024
Institute of Organic Chemistry of Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Here we present a highly versatile synthetic strategy based on twofold 6π-electrocyclization accompanied with HBr elimination as a novel approach towards centrosymmetric multi-heteroatom-doped nanographenes build around an electron-rich 1,4-dihydropyrrolo[3,2-b]pyrrole core. A straightforward synthesis from readily available substrates offers a unique possibility of fusing the 1,4-dihydropyrrolo[3,2-b]pyrrole subunit not only with carbocyclic building blocks, such as electron-deficient phenanthrenes, chrysenes, or [4]helicenes, but also with heterocyclic systems, such as benzo[b]furan and 5-thiatruxene. The clear advantage of this strategy is that there is no requirement to assemble complex scaffolds possessing bromoaryl units since bromine atom is introduced by bromination of 1,4-dihydropyrrolo[3,2-b]pyrrole core which, because of its exceptionally electron-rich character, is straightforward reaction.
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