Base-Promoted Tandem Synthesis of 2‑Azaaryl Tetrahydroquinolines

Base-Promoted Tandem Synthesis of 2‑Azaaryl Tetrahydroquinolines

A novel method to synthesize 2-azaaryl tetrahydroquinolines by the base-promoted tandem reaction of azaaryl methyl amines and styrene derivatives is reported (over 30 examples, yields up to 95%). Mechanistic probe experiments demonstrate that the deprotonation of the benzylic C–H bond and the additi...

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Veröffentlicht in:Organic letters 2021-03, Vol.23 (5), p.1594-1599
Hauptverfasser: Chen, Shuguang, Yang, Langxuan, Shang, Yongjia, Mao, Jianyou, Walsh, Patrick J
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel method to synthesize 2-azaaryl tetrahydroquinolines by the base-promoted tandem reaction of azaaryl methyl amines and styrene derivatives is reported (over 30 examples, yields up to 95%). Mechanistic probe experiments demonstrate that the deprotonation of the benzylic C–H bond and the addition to the styrene vinyl group proceeds via the SNAr mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c04306