Palladium-Catalyzed Selective CH Activation: A Simple Method to Synthesize C-3 Site Arylated Quinoline Derivatives
| Autor: | Xiajun Wang, Guosheng Huang, Zhaoyang Wu, Xiaoqiang Zhou, Chaowei Ma, Yongqin He, Xingxing Liu |
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| Rok vydání: | 2016 |
| Předmět: |
inorganic chemicals
010405 organic chemistry Ligand Migratory insertion Quinoline chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Reagent Organic chemistry Selectivity Silver carbonate Palladium |
| Zdroj: | Advanced Synthesis & Catalysis. 358:375-379 |
| ISSN: | 1615-4150 |
| DOI: | 10.1002/adsc.201500763 |
| Popis: | A novel protocol for the synthesis of 3-arylated quinoline derivatives has been developed using silver carbonate (Ag2CO3) and dioxygen (O-2) as the oxidants. In this method, quinolines acting as the parent reagent react with arenes under palladium acetate [Pd(OAc)(2)] catalysis along with 1-adamantanecarboxylic acid (Adm). The combination of the 1-adamantanecarboxylic acid ligand and the palladium catalyst is found to be an essential factor for achieving high activity and selectivity, and allows a wide range of 3-arylquinoline derivatives to be obtained in high yields. Moreover, a relevant mechanism is proposed, revealing that un der the palladium(II) catalysis a migratory insertion to C-3-H of quinolines and insertion to the C-H of arenes are key steps in this reaction. Mild reaction conditions and high selectivity of the reactive site provide potential for promising applications in drug discovery and functional materials. |
| Databáze: | OpenAIRE |
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