Silver-Promoted Synthesis of 5‑[(Pentafluorosulfanyl)methyl]-2-oxazolines

Silver-Promoted Synthesis of 5‑[(Pentafluorosulfanyl)methyl]-2-oxazolines

The synthesis of 5-[(pentafluorosulfanyl)­methyl]-2-oxazolines is reported. The use of a silver promoter allows the intramolecular cyclization of N-[2-chloro-3-(pentafluorosulfanyl)­propyl]­amide to occur without elimination of the chlorine atom, a reaction pathway typically observed for β-chloro-SF...

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Veröffentlicht in:Organic letters 2018-11, Vol.20 (22), p.7257-7260
Hauptverfasser: Gilbert, Audrey, Bertrand, Xavier, Paquin, Jean-François
Format: Artikel
Sprache:eng
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Zusammenfassung:The synthesis of 5-[(pentafluorosulfanyl)­methyl]-2-oxazolines is reported. The use of a silver promoter allows the intramolecular cyclization of N-[2-chloro-3-(pentafluorosulfanyl)­propyl]­amide to occur without elimination of the chlorine atom, a reaction pathway typically observed for β-chloro-SF5-alkyl compounds. The products, potentially valuable SF5-containing heterocycles, are obtained in up to 97% yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03170