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An unexpected reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and thiourea under photoinduced conditions

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Abstract

A photoinduced synthesis of S-aryl thiosulfonates through a three-component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and thiourea is achieved. The reaction scope generality with a range of aryldiazonium tetrafluoroborates is demonstrated. In this transformation, a radical coupling pathway is proposed with the insertion of sulfur dioxide in the presence of a photocatalyst under visible light irradiation. The organic sulfur motifs in S-aryl thiosulfonates originate from the convenient, cheap, and easily available thiourea and sodium metabisulfite.

Graphical abstract: An unexpected reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and thiourea under photoinduced conditions

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Publication details

The article was received on 21 Mar 2019, accepted on 06 Apr 2019 and first published on 11 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00410F
Citation: Org. Chem. Front., 2019, Advance Article

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    An unexpected reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and thiourea under photoinduced conditions

    X. Gong, X. Li, W. Xie, J. Wu and S. Ye, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00410F

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