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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 and Yunfei Du*

*School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China, Email: duyunfeiertju.edu.cn

B. Zhao, X. Li, X. Wang, L. Jiang, Z. Li, Y. Du, J. Org. Chem., 2023, 88, 1493-1503.

DOI: 10.1021/acs.joc.2c02480



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Abstract

Treatment of 2-alkenylanilines with phenyliodine(III) diacetate (PIDA) and LiBr or KI in HFIP provides the corresponding 3-bromoindoles and 3-iodoindoles via cascade oxidative cyclization/halogenation.

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proposed mechanisms



Key Words

indoles, PIDA


ID: J42-Y2023