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

Bingyue Zhao,Xiaoxian Li,Xiaofan Wang,Luchen Jiang,Zhe Li,Yunfei Du

The Journal of Organic Chemistry（2023）

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摘要

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.

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cascade oxidative cyclization/halogenation,synthesis

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