Visible Light-Driven\nInterrupted Barton Reaction:\nIntermolecular Radical-Relay Sulfonyloximation of Alkenes with DABSO\nand Alkyl Nitrites

A visible light-driven, intermolecular interrupted Barton\nreaction\nhas been developed for radical-relay sulfonyloximation of alkenes\nwith alkyl nitrites, using DABSO as a trapping reagent. This method\novercomes the challenges of competing normal Barton reactions and\npolarity mismatches by rapidly and irreversibly capturing alkyl radicals,\npreventing unwanted side reactions. The resulting polarity-reversed\nsulfonyl radicals undergo highly selective addition to alkenes, yielding\nα-alkylsulfonyl ketoximes tethered to hydroxyl or ketone groups.\nConducted under mild visible light conditions, this approach eliminates\nthe need for harsh mercury lamps, offering a scalable, chemoselective\nmethod for synthesizing valuable sulfonylated oxime derivatives.

Publication Details

Journal
Figshare
Published
2024-12-24
DOI
https://doi.org/10.1021/acs.orglett.4c04257.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Visible Light-Driven\nInterrupted Barton Reaction:\nIntermolecular Radical-Relay Sulfonyloximation of Alkenes with DABSO\nand Alkyl Nitrites

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Visible Light-Driven\nInterrupted Barton Reaction:\nIntermolecular Radical-Relay Sulfonyloximation of Alkenes with DABSO\nand Alkyl Nitrites

article en

Abstract

A visible light-driven, intermolecular interrupted Barton\nreaction\nhas been developed for radical-relay sulfonyloximation of alkenes\nwith alkyl nitrites, using DABSO as a trapping reagent. This method\novercomes the challenges of competing normal Barton reactions and\npolarity mismatches by rapidly and irreversibly capturing alkyl radicals,\npreventing unwanted side reactions. The resulting polarity-reversed\nsulfonyl radicals undergo highly selective addition to alkenes, yielding\nα-alkylsulfonyl ketoximes tethered to hydroxyl or ketone groups.\nConducted under mild visible light conditions, this approach eliminates\nthe need for harsh mercury lamps, offering a scalable, chemoselective\nmethod for synthesizing valuable sulfonylated oxime derivatives.

Figshare
Clean water and sanitation
Openalex Percentile: Top 60%
Mycorrhizal Fungi and Plant Interactions
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