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

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 var...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-02, Vol.55 (17), p.2489-2492
Main Authors: Ye, Shengqing, Li, Yuewen, Wu, Jie, Li, Zhiming
Format: Article
Language:English
Subjects:
Aromatic compounds
Halides
Light irradiation
NMR
Nuclear magnetic resonance
Spectrum analysis
Sulfonamides
Sulfones
Sulfur dioxide
Thioureas
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Summary: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. Thiourea dioxide is applied as the source of sulfonyl groups for the efficient synthesis of heteroaryl sulfones and sulfonamides from heteroaryl halides under visible light irradiation. This transformation proceeds through a radical process via heteroaryl sulfinate intermediates, as supported by EPR spectroscopy and DFT calculations.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc00008a