Photoredox-catalyzed intermolecular azidosulfonylation of alkenes with DABCO center dot(SO2)(2), trimethylsilyl azide and thianthrenium salts

A photoredox-catalyzed four-component reaction of alkenes, DABCO center dot(SO2)(2), trimethylsilyl azide and alkyl thianthrenium salts is described, providing a facile route to beta-azidosulfones in moderate to good yields with excellent regioselectivity under mild conditions. The thianthrenium sal...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 4; pp. 866 - 871
Main Authors Ma, Huiling, Li, Yanzhi, Wang, Peiqi, Ye, Jiamin, Zhang, Jun, Liu, Gang, Wu, Jie
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.02.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INSERTION
METABISULFITE
SULFONES
PHOTOINDUCED SYNTHESIS
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Summary:A photoredox-catalyzed four-component reaction of alkenes, DABCO center dot(SO2)(2), trimethylsilyl azide and alkyl thianthrenium salts is described, providing a facile route to beta-azidosulfones in moderate to good yields with excellent regioselectivity under mild conditions. The thianthrenium salts serving as general precursors of unstable alkyl radicals enable the synthesis of beta-azido alkylsulfones with diversity and efficiency. Additionally, this protocol can be further extended to other nucleophiles for the construction of different beta-functionalized sulfones. Moreover, the installed azide group can be easily converted to free amino and other valuable groups.
ISSN:2052-4129
DOI:10.1039/d2qo01706g