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Issue 16, 2018
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Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide under photocatalysis

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Abstract

Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide promoted by visible light is developed. The combination of 4-substituted pent-4-en-1-ols, DABCO·(SO2)2, and aryldiazonium tetrafluoroborates under mild conditions in the presence of a photocatalyst provides sulfonated 2,2-disubstituted tetrahydrofurans in moderate to good yields. Moreover, this protocol can be further extended to 5-phenylhex-5-en-1-ol and [2-(prop-1-en-2-yl)phenyl]methanol for the construction of sulfonyl-containing tetrahydropyran and 1,3-dihydroisobenzofuran derivatives. Preliminary mechanistic studies show that the arylsulfonyl radical is the key intermediate in the reaction process.

Graphical abstract: Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide under photocatalysis

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Publication details

The article was received on 30 May 2018, accepted on 03 Jul 2018 and first published on 04 Jul 2018


Article type: Research Article
DOI: 10.1039/C8QO00528A
Citation: Org. Chem. Front., 2018,5, 2437-2441
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    Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide under photocatalysis

    F. He, X. Cen, S. Yang, J. Zhang, H. Xia and J. Wu, Org. Chem. Front., 2018, 5, 2437
    DOI: 10.1039/C8QO00528A

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