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

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...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 11; pp. 1863 - 1867
Main Authors Gong, Xinxing, Li, Xiaofang, Xie, Wenlin, Wu, Jie, Ye, Shengqing
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.06.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
QUINOLINE N-OXIDES
3-COMPONENT SYNTHESIS
POTASSIUM METABISULFITE
SULFUR-DIOXIDE
CATALYZED SYNTHESIS
1,3-DIPOLAR CYCLOADDITION
SULFONYL HYDRAZIDES
DIARYLIODONIUM SALTS
STEREOSELECTIVE-SYNTHESIS
H BOND FUNCTIONALIZATION
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Summary: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.
ISSN:2052-4129
DOI:10.1039/c9qo00410f