Direct oxidative dearomatization of indoles: access to structurally diverse 2,2-disubstituted indolin-3-ones
Xigong Liu1, Xue Yan1, Yingde Tang1
1School of Biological Science and Technology, University of Jinan, Jinan 250022, P. R. China. 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.
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