Issue 34, 2024

Intermolecular radical oxyalkylation of arynes with alkenes and TEMPO

Abstract

Radical transformations with arynes represent an underexplored research field and only a few examples have been disclosed. In this research article, the implementation of arynes in three-component reactions with TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl) and activated alkenes is demonstrated. TEMPO is added to arynes, which triggers a Meerwein-type arylation cascade where the final alkyl radial is eventually trapped by a second equivalent of TEMPO. This method is applicable to activated alkenes such as electron-deficient acrylates, styrenes and also vinyl acetate to provide various bisalkoxyamines. This work is a contribution to the emerging field of radical aryne chemistry.

Graphical abstract: Intermolecular radical oxyalkylation of arynes with alkenes and TEMPO

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Article information

Article type
Edge Article
Submitted
02 Jul 2024
Accepted
25 Jul 2024
First published
26 Jul 2024
This article is Open Access

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

Chem. Sci., 2024,15, 13712-13716

Intermolecular radical oxyalkylation of arynes with alkenes and TEMPO

D. Bhattacharya, M. Scherübl, C. G. Daniliuc and A. Studer, Chem. Sci., 2024, 15, 13712 DOI: 10.1039/D4SC04369C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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