Metal‐Free Synthesis of (E)‐Vinyl Sulfones via An Insertion of Sulfur Dioxide/1,5‐Hydrogen Atom Transfer Sequence

A metal‐free three‐component reaction of propargyl alcohols, sodium metabisulfite, and aryldiazonium tetrafluoroborates under mild conditions is described. The reaction proceeds efficiently at room temperature without the need of any catalysts, affording the corresponding (E)‐vinyl sulfones in moder...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-11, Vol.362 (21), p.4744-4748
Main Authors: He, Fu‐Sheng, Yao, Yanfang, Xie, Wenlin, Wu, Jie
Format: Article
Language:English
Subjects:
1,5-hydrogen atom transfer
Alcohols
Functional groups
metal-free
Room temperature
Sodium metabisulfite
Sulfones
Sulfur dioxide
sulfur dioxide insertion
Vinyl radical
vinyl sulfones
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Summary:A metal‐free three‐component reaction of propargyl alcohols, sodium metabisulfite, and aryldiazonium tetrafluoroborates under mild conditions is described. The reaction proceeds efficiently at room temperature without the need of any catalysts, affording the corresponding (E)‐vinyl sulfones in moderate to good yields with excellent functional group tolerance. Preliminary mechanistic studies show that a vinyl radical‐induced 1,5‐hydrogen atom transfer process and functional group migration are involved, resulting in the cleavage of inert C−H and C−C bonds in sequence.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000778