Sponsor
This work was supported by the National Science Foundation under Grant No. 2247802. The NSF provided instrument funding for the BioAnalytical Mass Spectrometry Facility at PSU under Grant No. 1828753.
Published In
Chemical Science
Document Type
Article
Publication Date
12-2023
Subjects
Arynes, Organic chemistry, synthesis
Abstract
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.
Rights
Open Access Article
This Open Access Article is licensed under a
Creative Commons Attribution 3.0 Unported Licence
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DOI
10.1039/D3SC05429B
Persistent Identifier
https://archives.pdx.edu/ds/psu/41006
Citation Details
Metze, B., Roberts, R. A., Nilova, A., & Stuart, D. R. (2023). An efficient and chemoselective method to generate arynes. Chemical Science.