Issue 10, 2022

Transition-metal-free oxindole synthesis: quinone–K2CO3 catalyzed intramolecular radical cyclization

Abstract

A novel and highly efficient transition-metal-free approach for the conversion of α-bromoanilides to 3,3-disubstituted oxindoles is described. This transformation is promoted by a catalytic amount of 9,10-phenanthrenequinone (PQ) together with K2CO3, and exhibits good functional group tolerance. Mechanistic investigations revealed that the reaction is most likely a radical process, possibly initiated by single electron transfer from complexes formed by PQ and K2CO3, to generate the tertiary radical intermediate.

Graphical abstract: Transition-metal-free oxindole synthesis: quinone–K2CO3 catalyzed intramolecular radical cyclization

Supplementary files

Article information

Article type
Research Article
Submitted
07 feb 2022
Accepted
04 apr 2022
First published
05 apr 2022

Org. Chem. Front., 2022,9, 2593-2599

Transition-metal-free oxindole synthesis: quinone–K2CO3 catalyzed intramolecular radical cyclization

S. Wu, Q. Zhao, C. Wu, C. Wang and H. Lei, Org. Chem. Front., 2022, 9, 2593 DOI: 10.1039/D2QO00205A

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