Cu(OTf)(2)-mediated C(sp(2))-H arylsulfonylation of enamides via the insertion of sulfur dioxide

An efficient and straightforward three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp(2))-H arylsulfonylation of enamides has been developed. This Cu(OTf)(2)-mediated SO2 insertion reaction proceeds...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 1; pp. 94 - 98
Main Authors Zhu, Tong-Hao, Zhang, Xiao-Chen, Zhao, Kai, Loh, Teck-Peng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.01.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
3-COMPONENT REACTION
SULFONYLATION
CHEMISTRY
DIARYLIODONIUM SALTS
CYCLIC ENAMIDES
STEREOSELECTIVE-SYNTHESIS
C-H BONDS
METAL-FREE
AMINOSULFONYLATION
CATALYZED DIRECT ARYLATION
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Summary:An efficient and straightforward three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp(2))-H arylsulfonylation of enamides has been developed. This Cu(OTf)(2)-mediated SO2 insertion reaction proceeds smoothly to afford a diverse range of -amidovinyl sulfones bearing manifold functional groups in moderate to excellent yields with high regio- and stereoselectivities.
ISSN:2052-4129
DOI:10.1039/c8qo01144c