Synthesis of 3‑Haloindoles via Cascade Oxidative Cyclization/Halogenation of 2‑Alkenylanilines Mediated by PIDA and LiBr/KI

Synthesis of 3‑Haloindoles via Cascade Oxidative Cyclization/Halogenation of 2‑Alkenylanilines Mediated by PIDA and LiBr/KI

The treatment of 2-alkenylanilines with phenyliodine­(III) diacetate (PIDA) and LiBr or KI in HFIP was found to afford the corresponding 3-haloindoles via cascade oxidative cyclization/halogenation encompassing oxidative C–N/C–X (X = Br, I) bond formations. A plausible mechanism involving the in sit...

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Veröffentlicht in:Journal of organic chemistry 2023-02, Vol.88 (3), p.1493-1503
Hauptverfasser: Zhao, Bingyue, Li, Xiaoxian, Wang, Xiaofan, Jiang, Luchen, Li, Zhe, Du, Yunfei
Format: Artikel
Sprache:eng
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Zusammenfassung:The treatment of 2-alkenylanilines with phenyliodine­(III) diacetate (PIDA) and LiBr or KI in HFIP was found to afford the corresponding 3-haloindoles via cascade oxidative cyclization/halogenation encompassing oxidative C–N/C–X (X = Br, I) bond formations. A plausible mechanism involving the in situ formation of the reactive AcO-X (X = Br, I) from the reaction of PIDA and LiBr/KI was postulated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02480