C-H arylations were accomplished with a user-friendly heterogeneous palladium catalyst in the biomass-derived γ-valerolactone (GVL) as an environmentally-benign reaction medium. The user-friendly protocol was characterized by ample substrate scope and high functional group tolerance in the C-H arylation of 1,2,3-triazoles, and the palladium catalyst could be recycled and reused in the C-H activation process.
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http://dx.doi.org/10.1039/c6cc03468c | DOI Listing |
Beilstein J Org Chem
December 2024
Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan.
The C-H arylation of 2-quinolinecarboxyamide bearing a C-Br bond at the -aryl moiety is carried out with a palladium catalyst. The reaction proceeds at the C-H bond on the pyridine ring adjacent to the amide group in the presence of 10 mol % Pd(OAc) at 110 °C to afford the cyclized product in 42% yield. The yield is improved to 94% when the reaction is performed with PPh as a ligand of palladium.
View Article and Find Full Text PDFSynthesis (Stuttg)
January 2024
Department of Chemistry, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, USA.
alkaloid complanadine A, isolated by Kobayashi et al. in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatment for neurodegenerative disorders and persistent pain management.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
Herein, we introduce a mild and efficient method for synthesizing aniline biaryls and unsymmetrical phenol biaryls through iodine-catalyzed coupling of quinone imine ketals (QIKs)/quinonemonoacetals (QMAs) and -naphthols. This approach allows for the unusual formation of ortho-substituted anilines and phenols, valuable in pharmaceuticals and advanced materials but typically difficult to produce. Our method achieves high -selectivity without needing transition metals or external/internal templates.
View Article and Find Full Text PDFJ Org Chem
December 2024
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China.
We reported a palladium/norbornene-catalyzed dual intermolecular C-H arylation/intramolecular cyclization reaction of iodoferrocenes with -bromobenzamides, enabling the formation of arylated isoquinolone-fused ferrocenes in a straightforward and effective manner. This method has a broad substrate scope and good functional group compatibility, while the gram-scale reaction demonstrates the practicality of this method.
View Article and Find Full Text PDFOrg Lett
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.
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