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Issue 17, 2019
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Thiourea dioxide as a source of sulfonyl groups: photoredox generation of sulfones and sulfonamides from heteroaryl/aryl halides

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Abstract

Thiourea dioxide as the source of sulfonyl groups for the efficient synthesis of heteroaryl sulfones and sulfonamides from heteroaryl halides under visible light irradiation is reported. This transformation proceeds smoothly via heteroaryl sulfinate intermediates, which can be trapped in situ by various electrophiles. A broad reaction scope is demonstrated, especially for the electron-deficient heteroaryl halides. Mechanistic studies show that the radical coupling of the heteroaryl radical and sulfur dioxide radical anion may be the key step during the reaction process, as supported by EPR spectroscopy and DFT calculations.

Graphical abstract: Thiourea dioxide as a source of sulfonyl groups: photoredox generation of sulfones and sulfonamides from heteroaryl/aryl halides

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Publication details

The article was received on 01 Jan 2019, accepted on 04 Feb 2019 and first published on 04 Feb 2019


Article type: Communication
DOI: 10.1039/C9CC00008A
Citation: Chem. Commun., 2019,55, 2489-2492

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    Thiourea dioxide as a source of sulfonyl groups: photoredox generation of sulfones and sulfonamides from heteroaryl/aryl halides

    S. Ye, Y. Li, J. Wu and Z. Li, Chem. Commun., 2019, 55, 2489
    DOI: 10.1039/C9CC00008A

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