Direct Oxidative Dearomatization of Indoles with Aromatic Ketones: Rapid Access to 2,2-Disubstituted Indolin-3-ones

Jiarun Liu, Jiancheng Huang, Kuiyong Jia, Tianxing Du, Changyin Zhao, Rongxiu Zhu*, Xigong Liu*

*School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China, Email: rxzhusdu.edu.cn, 201990000024sdu.edu.cn

J. Liu, J. Huang, K. Jia, T. Du, C. Zhao, R. Zhu, X. Liu, Synthesis, 2020, 52, 763-768.

DOI: 10.1055/s-0039-1691528

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Abstract

A TEMPO oxoammonium salt mediates a metal-free oxidative dearomatization of indoles with aromatic ketones in the presence of H₂SO₄ to provide 2,2-disubstituted indolin-3-ones in good yields. The dearomatization proceeds smoothly and displays a broad substrate scope with respect to both indoles and aromatic ketones.

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Key Words

indoles, 3-oxindoles, TEMPO

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ID: J66-Y2020