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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 6
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Articles

Ru-catalyzed oxidative dearomatization-alkoxylation of N-Boc indoles

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Pages 943-951 | Received 22 Oct 2020, Published online: 04 Jan 2021
 

Abstract

Ruthenium catalyzed oxidative dearomatization-alkoxylation of N-Boc indoles for the synthesis of 2-alkoxyindolin-3-ones was described. The N-Boc indoles can be transformed into 2-alkoxyindolin-3-ones with RuCl3·3H2O as catalyst and tert-butyl hydroperoxide (TBHP, 3.0 equiv) as oxidant in dichloromethane/alcohol. Furtherly, the mechanism had been proposed on the basis of control experiments and isolation of intermediates.

Graphical Abstract

Disclosure statement

No potential conflict of interest was reported by the author(s).

Supporting information

Full experimental detail, 1H and 13C NMR spectra. This material can be found via the “Supplementary Content” section of this article’s webpage.

Additional information

Funding

The work was supported by the Foundation of Guizhou Educational Committee [Grant No. qianjiaohe KY zi [2019] 081], the Natural Science Foundation of Guizhou Province [Grant No. qiankehejichu [2018] number 1141] and the Natural Science Foundation of Liupanshui City [Grant No. 52020-2018-04-10].

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