Issue 15, 2022

Redox-neutral access to 3,3′-disubstituted oxindoles via radical coupling reactions

Abstract

One of the most straightforward strategies for organic synthesis is a visible-light-induced direct coupling between donor and acceptor substrates of a productive EDA complex. In this paper, we report the results of using EDA complexes of in situ formed enolates with redox-active esters for radical-coupling reactions under mild conditions (metal-, photocatalyst-, and base-free). The leaving group from the substrate in these experiments was reused as a base in the reaction. This strategy can successfully be applied to a wide variety of primary, secondary, and tertiary alkyl radical precursors and oxindoles in radical-coupling reactions. The success of sunlight-driven transformation and gram-level synthesis via flow chemistry delivered promising results for further application in industrial settings. Mechanistic investigation, including control experiments, and UV-vis spectroscopy provided insight into the mechanism.

Graphical abstract: Redox-neutral access to 3,3′-disubstituted oxindoles via radical coupling reactions

Supplementary files

Article information

Article type
Research Article
Submitted
07 Apr 2022
Accepted
13 Jun 2022
First published
30 Jun 2022

Org. Chem. Front., 2022,9, 4164-4170

Redox-neutral access to 3,3′-disubstituted oxindoles via radical coupling reactions

C. Lu, D. Jing, Y. Shen, J. Luo and K. Zheng, Org. Chem. Front., 2022, 9, 4164 DOI: 10.1039/D2QO00570K

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