Visible Light-Driven Interrupted Barton Reaction: Intermolecular Radical-Relay Sulfonyloximation of Alkenes with
Wei Li1, Lingtong Zhao1, Chenchen Diao1
1State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China.
Abstract:
A visible light-driven, intermolecular interrupted Barton reaction has been developed for radical-relay sulfonyloximation of alkenes with alkyl nitrites, using DABSO as a trapping reagent. This method overcomes the challenges of competing normal Barton reactions and polarity mismatches by rapidly and irreversibly capturing alkyl radicals, preventing unwanted side reactions. The resulting polarity-reversed sulfonyl radicals undergo highly selective addition to alkenes, yielding α-alkylsulfonyl ketoximes tethered to hydroxyl or ketone groups. Conducted under mild visible light conditions, this approach eliminates the need for harsh mercury lamps, offering a scalable, chemoselective method for synthesizing valuable sulfonylated oxime derivatives.
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