Issue 47, 2023

An efficient and chemoselective method to generate arynes


Arynes hold immense potential as reactive intermediates in organic synthesis as they engage in a diverse range of mechanistically distinct chemical reactions. However, the poor functional group compatibility of generating arynes or their precursors has stymied their widespread use. Here, we show that generating arynes by deprotonation of an arene and elimination of an “onium” leaving group is mild, efficient and broad in scope. This is achieved by using aryl(TMP)iodonium salts (TMP = 2,4,6-trimethoxyphenyl) as the aryne precursor and potassium phosphate as the base, and a range of arynophiles are compatible. Additionally, we have performed the first quantitative analysis of functional group compatibility for several methods to generate arynes, including the method developed here and the current state of the art. Finally, we show that a range of “sensitive” functional groups such as Lewis and Brønsted acids and electrophiles are compatible under our conditions.

Graphical abstract: An efficient and chemoselective method to generate arynes

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Article information

Article type
Edge Article
12 Oct 2023
16 Nov 2023
First published
17 Nov 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 license

Chem. Sci., 2023,14, 13885-13892

An efficient and chemoselective method to generate arynes

B. E. Metze, R. A. Roberts, A. Nilova and D. R. Stuart, Chem. Sci., 2023, 14, 13885 DOI: 10.1039/D3SC05429B

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