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

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. Mec...

Full description

Saved in:
Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (10), p.2593-2599
Main Authors: Wu, Shiyuan, Zhao, Qiuting, Wu, Chao, Wang, Chengming, Hao Lei
Format: Article
Language:English
Subjects:
Chemical synthesis
Electron transfer
Functional groups
Organic chemistry
Potassium carbonate
Quinones
Single electrons
Transition metals
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00205a