Synthesis of Sulfonyl‐Containing spirotrienones from Sodium Metabisulfite

An efficient three‐component reaction of biaryl ynones, sodium metabisulfite and aryldiazonium tetrafluoroborates is developed. The reaction occurs at room temperature without any additives, thus offering a sustainable approach to access sulfonyl‐containing spiro[5,5]trienones. This protocol feature...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-07, Vol.366 (13), p.3041-3045
Main Authors: Xiao, Wei, Tang, Zhimei, Fu‐Sheng He, Wu, Jie
Format: Article
Language:English
Subjects:
Chemical synthesis
Functional groups
Room temperature
Sodium metabisulfite
Substrates
Sulfur dioxide
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Summary:An efficient three‐component reaction of biaryl ynones, sodium metabisulfite and aryldiazonium tetrafluoroborates is developed. The reaction occurs at room temperature without any additives, thus offering a sustainable approach to access sulfonyl‐containing spiro[5,5]trienones. This protocol features mild conditions, broad substrate scope and high functional group compatibility, furnishing the target products in moderate to good yields. Mechanistic studies indicate that the reaction undergoes a 6‐exo‐trig dearomative spirocyclization process which is initated by an aryl radical with the insertion of sulfur dioxide.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400345