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

Abstract

Ruthenium catalyzed oxidative dearomatization-hydroxylation of N-Boc indoles for the synthesis of 2-hydroxyindolin-3-ones was described. The N-Boc indoles can be transformed into 2-hydroxyindolin-3-ones with RuCl₃·3H₂O as catalyst, p-toluenesulfonic acid (TsOH·H₂O) as promoter and tert-butyl peroxide (TBHP, 3.0 equiv) as oxidant in acetonitrile. The mechanism had been proposed on the basis of control experiments and isolation of intermediate.

Graphical Abstract

Keywords:

• Ruthenium
• oxidative dearomatization
• indoles
• indolin-3-ones
• TBHP

Additional information

Funding

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