A novel copper-catalyzed C-H arylation of heteroarenes with anilines by an in situ diazonium reaction is established by using silver nitrite (AgONO) as an unconventional nitrosating reagent under acid-free conditions. It provides a complementary approach for the C-H arylation of electron-rich heteroarenes with aromatic amines affording a variety of heterobiaryls in moderate to good yields.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201403640 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Intermediate Control: Unlocking Hitherto Unknown Reactivity and Selectivity in N-Conjugated Allenes and Alkynes.
Acc Chem Res
January 2025
Department of Chemistry and Chemistry Institution for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
ConspectusControlling selectivity through manipulation of reaction intermediates remains one of the most enduring challenges in organic chemistry, providing novel solutions for selective C-C π-bond functionalization. This approach, guided by activation principles, provides an effective method for selective functional group installation, enabling direct synthesis of organic molecules that are inaccessible through conventional pathways. In particular, the selective functionalization of N-conjugated allenes and alkynes has emerged as a promising research focus, driven by advances in controlling reactive intermediates and activation strategies.
View Article and Find Full Text PDFSynthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[]fluoranthenes via a Pd-catalyzed Suzuki-Miyaura/C-H arylation cascade.
Beilstein J Org Chem
December 2024
Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye.
Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45-90%). This cascade involves an initial Suzuki-Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C-H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[]fluoranthenes, which are all structurally relevant to benzo[]fluoranthene-based fungal natural products.
View Article and Find Full Text PDFPd(OAc)-Catalyzed Synthesis of Imidazo[1,2-]phenanthridines via a Sequential Ullmann Coupling and Oxidative Coupling Dehydrogenation.
J Org Chem
January 2025
School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.
The Ullmann coupling and oxidative coupling dehydrogenation reactions have occurred sequentially, catalyzed by Pd(OAc), which unexpectedly yielded fused imidazo[1,2-]phenanthridine derivatives in good to high yields. Structural analysis of the intermediate and final products indicated that the protocol did not include C-H and N-H arylation.
View Article and Find Full Text PDFIntramolecular C-H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds.
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 PDFConcise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing.
Synthesis (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 PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!