Synlett
DOI: 10.1055/s-0036-1589106
letter
© 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: weiwenting@nbu.edu.cn
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.
Further Information

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.

Abstract

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.

Supporting Information