Issue 46, 2019
From the journal:

Chemical Communications

Direct oxidative dearomatization of indoles: access to structurally diverse 2,2-disubstituted indolin-3-ones†

Xigong Liu,a   Xue Yan,a   Yingde Tang,a   Cheng-Shi Jiang, ORCID logo a   Jin-Hai Yu,a   Kaiming Wanga  and  Hua Zhang ORCID logo *a  

* Corresponding authors

a School of Biological Science and Technology, University of Jinan, Jinan 250022, P. R. China
E-mail: bio_zhangh@ujn.edu.cn

Abstract

Described is an efficient oxidative dearomatization of indoles with TEMPO oxoammonium salt and a broad range of nucleophiles. Under very mild conditions, dearomative oxyalkynylation and oxyalkenylation of indoles to structurally diverse 2,2-disubstituted indolin-3-ones were developed for the first time with high atom-economy. In addition, dearomative oxyarylation, oxyallylation, and oxycyanation of indoles were also demonstrated. Mechanism studies indicated that TEMPO oxoammonium salt served as the sole oxidant source through an electron donor–acceptor (EDA) intermediate.

Graphical abstract: Direct oxidative dearomatization of indoles: access to structurally diverse 2,2-disubstituted indolin-3-ones

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Article information

DOI
https://doi.org/10.1039/C9CC02956G
Article type
Communication
Submitted
16 Apr 2019
Accepted
14 May 2019
First published
14 May 2019

Chem. Commun., 2019,55, 6535-6538

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Direct oxidative dearomatization of indoles: access to structurally diverse 2,2-disubstituted indolin-3-ones

X. Liu, X. Yan, Y. Tang, C. Jiang, J. Yu, K. Wang and H. Zhang, Chem. Commun., 2019, 55, 6535 DOI: 10.1039/C9CC02956G

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