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Aminofluorosulfonylation of β,γ-Unsaturated Hydrazones with Sulfur Dioxide and N-Fluorobenzenesulfonimide: Accessing Pyrazoline-Functionalized Aliphatic Sulfonyl Fluorides
- Source :
- Organic Letters; June 2023, Vol. 25 Issue: 21 p3910-3915, 6p
- Publication Year :
- 2023
-
Abstract
- An efficient aminofluorosulfonylation strategy was developed for the synthesis of various pyrazoline-functionalized aliphatic sulfonyl fluorides using β,γ-unsaturated hydrazones with sulfur dioxide and NFSI as the starting materials under mild conditions. The sulfonyl fluoride products could be successfully transformed into the corresponding sulfonate esters and amides via the sulfur(VI) fluoride exchange (SuFEx) click reactions. Preliminary mechanistic investigations demonstrate that the reaction operates through a radical cyclization/SO2insertion/fluorination cascade process.
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Volume :
- 25
- Issue :
- 21
- Database :
- Supplemental Index
- Journal :
- Organic Letters
- Publication Type :
- Periodical
- Accession number :
- ejs63110814
- Full Text :
- https://doi.org/10.1021/acs.orglett.3c01278