Photoredox-Enabled Radical Ring-Opening Fluorosulfonamidation/Fluorosulfonylmethylation of Methylenecyclobutanols

We report a photoredox strategy for radical-initiated ring-opening fluorosulfonamidation/fluorosulfonylmethylation of methylenecyclobutanols using NFSAP (<i>N</i>-fluorosulfamoylpyridinium salts) and BMSF (bromomethylsulfonyl fluoride) as the respective radical sources. This approach provides efficient access to FSO<sub>2</sub>CH<sub>2</sub>-/FSO<sub>2</sub>N-functionalized γ,δ-unsaturated carbonyl compounds─both FSO<sub>2</sub>CH<sub>2</sub>-/FSO<sub>2</sub>N and γ,δ-unsaturated carbonyl motifs are useful structural scaffolds─while offering good scalability and broad compatibility with postderivatization reactions.

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Publication Details

Journal
Organic Letters
Published
2026-02-13
DOI
https://doi.org/10.1021/acs.orglett.6c00017
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Photoredox-Enabled Radical Ring-Opening Fluorosulfonamidation/Fluorosulfonylmethylation of Methylenecyclobutanols

Qi Lin, Hui Li, Xiaoxing Li, Ni-Ping Pei et al.
Organic Letters
Radical Photochemical Reactions
article

Photoredox-Enabled Radical Ring-Opening Fluorosulfonamidation/Fluorosulfonylmethylation of Methylenecyclobutanols

Qi Lin, Hui Li, Xiaoxing Li, Ni-Ping Pei, Li-Jing Wang, Ye-Pu Fu, Wei Li, Lele Zhang
article en

Abstract

We report a photoredox strategy for radical-initiated ring-opening fluorosulfonamidation/fluorosulfonylmethylation of methylenecyclobutanols using NFSAP (<i>N</i>-fluorosulfamoylpyridinium salts) and BMSF (bromomethylsulfonyl fluoride) as the respective radical sources. This approach provides efficient access to FSO<sub>2</sub>CH<sub>2</sub>-/FSO<sub>2</sub>N-functionalized γ,δ-unsaturated carbonyl compounds─both FSO<sub>2</sub>CH<sub>2</sub>-/FSO<sub>2</sub>N and γ,δ-unsaturated carbonyl motifs are useful structural scaffolds─while offering good scalability and broad compatibility with postderivatization reactions.

Organic LettersVol. 28(8)
Ministry of Education of the People's Republic of China (CN), Hebei University (CN)
Openalex Percentile: Top 55%
Radical Photochemical Reactions
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