Pd-Catalyzed Tandem Reaction of 2-Aminostyryl Nitriles with Arylboronic Acids: Synthesis of 2-Arylquinolines
| Autor: | Yinlin Shao, Ling Dai, Shulin Yu, Jiuxi Chen, Xu Tong, Tianxing Cheng |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Nucleophilic addition
Nitrile 010405 organic chemistry Aryl Organic Chemistry Quinoline chemistry.chemical_element 010402 general chemistry Condensation reaction 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Cascade reaction Palladium |
| Zdroj: | The Journal of Organic Chemistry. 84:13604-13614 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.9b01875 |
| Popis: | A novel palladium-catalyzed protocol for the synthesis of 2-arylquinolines via tandem reaction of 2-aminostyryl nitriles with arylboronic acids has been developed with good functional group tolerance. The presented approach offers a new synthetic pathway toward the core structures of 2-arylquinolines compared to classical condensation reaction of (E)-2-aminostyryl aryl ketones. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular cyclization and dehydration to quinoline ring. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|