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

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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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Publication details

The article was received on 16 Apr 2019, accepted on 14 May 2019 and first published on 14 May 2019


Article type: Communication
DOI: 10.1039/C9CC02956G
Chem. Commun., 2019, Advance Article

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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, Advance Article , DOI: 10.1039/C9CC02956G

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