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

doi:10.1021/acs.joc.2c02480

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

J Org Chem. 2023 Feb 3;88(3):1493-1503. doi: 10.1021/acs.joc.2c02480. Epub 2023 Jan 11.

Authors

Bingyue Zhao¹, Xiaoxian Li¹, Xiaofan Wang¹, Luchen Jiang¹, Zhe Li¹, Yunfei Du¹

Affiliation

¹ School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.

PMID: 36631394
DOI: 10.1021/acs.joc.2c02480

Abstract

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.