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Photoinduced synthesis of allylic sulfones using potassium metabisulfite as the source of sulfur dioxide

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Abstract

Synthesis of allylic sulfones through a photoinduced three-component reaction of aryl/alkyl halides, potassium metabisulfite, and allylic bromides under ultraviolet irradiation at room temperature is developed. Diverse allylic sulfones are generated in moderate to good yields without the addition of any metals or photoredox catalysts. Different functional groups, including amino, ester, cyano, trifluoromethyl, and chloro are compatible under the conditions. Not only aryl halides but also alkyl halides are workable in the transformation. During this process, the natural abundant potassium metabisulfite is used as the source of sulfur dioxide. A plausible mechanism which involves the photoinduced C–X bond dissociation, sulfur dioxide fixation, and addition of the sulfonyl radical to allylic bromide is proposed.

Graphical abstract: Photoinduced synthesis of allylic sulfones using potassium metabisulfite as the source of sulfur dioxide

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Publication details

The article was received on 29 Sep 2018, accepted on 08 Nov 2018 and first published on 08 Nov 2018


Article type: Research Article
DOI: 10.1039/C8QO01048J
Citation: Org. Chem. Front., 2019, Advance Article
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    Photoinduced synthesis of allylic sulfones using potassium metabisulfite as the source of sulfur dioxide

    J. Zhang, K. Zhou, G. Qiu and J. Wu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01048J

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