An Unexpected Reaction between Diaryliodonium Salts and DMSO
Konrad Kepski, Wesley James Moran
Organics · pp. 275–280 · Published 31 Aug 2022
10.3390/org3030020Abstract
Diaryliodonium salts are useful arylating reagents that have been exploited widely. In this Communication, we demonstrate that heating diphenyliodonium triflate in the solvent DMSO leads to an unexpected arylation reaction. It is postulated that arylation of DMSO at oxygen, followed by a thia-Sommelet–Hauser rearrangement, leads to the formation of 2-thiomethylphenols. More substituted diaryliodonium salts and cyclic diaryliodonium salts are shown to be more stable and less likely to react with DMSO. In conclusion, when using iodonium salts dissolved in DMSO, beware of side-reactions.
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Cited by 8
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Showing 4 of 8 known citations — external sources report more than can currently be individually listed.
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