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Issue 21, 2018
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Photoinduced synthesis of (E)-vinyl sulfones through the insertion of sulfur dioxide

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Abstract

Under visible light irradiation, a three-component reaction of potassium alkyltrifluoroborates, sulfur dioxide and alkynes with the assistance of photocatalysis and in the presence of copper(II) triflate is described. This transformation affords (E)-vinyl sulfones efficiently with excellent regioselectivity and stereoselectivity under mild conditions. Various functional groups including acetyl and thiophenyl groups are tolerated. The photocatalysis facilitates the formation of an alkyl radical, which initiates the transformation with the insertion of sulfur dioxide. The presence of the copper catalyst assists the addition of an alkylsulfonyl radical to alkyne, thus leading to (E)-vinyl sulfones.

Graphical abstract: Photoinduced synthesis of (E)-vinyl sulfones through the insertion of sulfur dioxide

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Publication details

The article was received on 05 Sep 2018, accepted on 27 Sep 2018 and first published on 28 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00965A
Citation: Org. Chem. Front., 2018,5, 3153-3157
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    Photoinduced synthesis of (E)-vinyl sulfones through the insertion of sulfur dioxide

    T. Liu, Y. Ding, X. Fan and J. Wu, Org. Chem. Front., 2018, 5, 3153
    DOI: 10.1039/C8QO00965A

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