Issue 4, 2023

Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles

Abstract

The synthetic application of (hetero)aryl radicals in organic synthesis has been known since the last century. However, their applicability has significantly suffered from ineffective generation protocols. Herein, we present a visible-light-induced transition metal-free (hetero)aryl radical generation from readily available (hetero)aryl halides for the synthesis of 3,3′-disubstituted oxindoles. This transformation is amenable to a wide range of (hetero)aryl halides as well as several easily accessible acrylamides, and it is also scalable to multigram synthesis. Finally, the versatility of the oxindole products is demonstrated through their conversion to a variety of useful intermediates applicable to target-directed synthesis.

Graphical abstract: Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Oct 2022
Accepted
19 Dec 2022
First published
03 Jan 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 897-902

Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles

J. Majhi, A. Granados, B. Matsuo, V. Ciccone, R. K. Dhungana, M. Sharique and G. A. Molander, Chem. Sci., 2023, 14, 897 DOI: 10.1039/D2SC05918E

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