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Electrophilic Reagents for the Direct Incorporation of Uncommon SCF₂CF₂H and SCF₂CF₃ Motifs.

ABSTRACT: The introduction of fluoroalkylthioether groups has attracted the attention of the drug-discovery community given the special physicochemical and pharmacokinetic features they confer to bioactive compounds, yet these are often limited to standard SCF₃ and SCF₂H moieties. Herein, two saccharin-based electrophilic reagents have been disclosed for the incorporation of uncommon SCF₂CF₂H and SCF₂CF₃ motifs. Their reactivity performance, multigram-scale preparation, and divergent derivatization have been thoroughly investigated with a variety of nucleophiles, including natural products and pharmaceuticals.

SUBMITTER: Mestre J

PROVIDER: S-EPMC9400389 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Electrophilic Reagents for the Direct Incorporation of Uncommon SCF2CF2H and SCF2CF3 Motifs.

Mestre Jordi J Bernús Miguel M Castillón Sergio S Boutureira Omar O

The Journal of organic chemistry 20220809 16

The introduction of fluoroalkylthioether groups has attracted the attention of the drug-discovery community given the special physicochemical and pharmacokinetic features they confer to bioactive compounds, yet these are often limited to standard SCF3 and SCF2H moieties. Herein, two saccharin-based electrophilic reagents have been disclosed for the incorporation of uncommon SCF2CF2H and SCF2CF3 motifs. Their reactivity performance ...[more]

PMID: 35944166

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