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

Autor: Liu, Xigong, Yan, Xue, Tang, Yingde, Jiang, Cheng-Shi, Yu, Jin-Hai, Wang, Kaiming, Zhang, Hua
Předmět:
Zdroj: Chemical Communications; 6/11/2019, Vol. 55 Issue 46, p6535-6538, 4p
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index