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Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

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Abstract

Metal-free insertion of sulfur dioxide with aryl iodides and silyl enolates or allylic bromide under ultraviolet irradiation at room temperature is accomplished. This protocol provides a convenient route to sulfonated cyclic compounds under mild conditions. Not only N-(2-iodophenyl)-N-methylmethacrylamides but also 1-iodo-2-allenoxybenzene is workable. A plausible mechanism is proposed, which shows that during the reaction process, aryl radicals formed in situ from aryl iodides under ultraviolet irradiation undergo intramolecular 5-exo-cyclization, with subsequent sulfonylation via insertion of sulfur dioxide. The resulting sulfonyl radicals are further trapped by silyl enolates or allylic bromide giving rise to sulfonated cyclic compounds.

Graphical abstract: Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

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Publication details

The article was received on 22 Oct 2019, accepted on 06 Nov 2019 and first published on 06 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01274E
Org. Chem. Front., 2020, Advance Article

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    Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

    S. Ye, K. Zhou, P. Rojsitthisak and J. Wu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01274E

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