Pd-Catalyzed Tandem Reaction of 2‑Aminostyryl Nitriles with Arylboronic Acids: Synthesis of 2‑Arylquinolines

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-arylquinoline...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-11, Vol.84 (21), p.13604-13614
Main Authors: Xu, Tong, Shao, Yinlin, Dai, Ling, Yu, Shulin, Cheng, Tianxing, Chen, Jiuxi
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01875