DOI: 10.1055/s-0036-1589106
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Indoline-2,3-diones by Radical Coupling of Indolin-2-ones with tert-Butyl Hydroperoxide

Wei-Wei Ying ◊, Wen-Ming Zhu ◊, Hongze Liang, Wen-Ting Wei*
  • School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email:
This research is sponsored by research funds of NBU (No. ZX2016000706), the foundation of Ningbo University (No. XYL17009), and the K. C. Wong Magna Fund in Ningbo University.
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Publication History

Received: 23 July 2017

Accepted after revision: 22 August 2017

Publication Date:
14 September 2017 (eFirst)

These authors contributed equally to this work.


A novel strategy has been developed for the synthesis of indoline-2,3-diones through a metal-free radical-coupling reaction. Alkyl radicals derived from indolin-2-ones through a radical-transfer reaction combine with the tert-butylhydroperoxy radical readily generated from commercially available tert-butyl hydroperoxide to afford 3-(tert-­butylperoxy)indolin-2-one intermediates that can be further transformed into indoline-2,3-diones under air. This strategy provides a ­simple and efficient route to the construction of a C=O bond without the use of any metal catalyst or base.

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