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

doi:10.1055/s-0039-1691528

Synthesis, Table of Contents

Synthesis 2020; 52(05): 763-768
DOI: 10.1055/s-0039-1691528

paper

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∗

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

,

Xigong Liu∗

› Author Affiliations

Abstract

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^§ These authors contributed equally to this work

Abstract

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

Key words

indole - oxidative - dearomatization - aromatic ketone - 2,2-disubstituted indolin-3-one

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References

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