Base-catalyzed stereoselective hydrophenoxylation and hydrothiolation of hexafluorobutyne

Base-catalyzed stereoselective hydrophenoxylation and hydrothiolation of hexafluorobutyne

[Display omitted] •Two-phase reaction.•Mild reaction conditions.•High Z selectivity.•100% Atom utilization. Novel base-catalyzed hydrophenoxylation and hydrothiolation of hexafluorobutyne are described. By using an easily available base, a variety of vinyl ethers as well as sulfides are prepared at...

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Veröffentlicht in:Tetrahedron letters 2020-03, Vol.61 (13), p.151693, Article 151693
Hauptverfasser: Bo, Zhao, Ji-Jun, Zeng, Sheng, Han, Dong-Huai, Tu, Jiang-Wei, Li, Wei, Zhang, Jian, Lu
Format: Artikel
Sprache:eng
Schlagworte:
Base-catalyzed
Hydrophenoxylation
Hydrothiolation
Nucleophilic addition
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Zusammenfassung:[Display omitted] •Two-phase reaction.•Mild reaction conditions.•High Z selectivity.•100% Atom utilization. Novel base-catalyzed hydrophenoxylation and hydrothiolation of hexafluorobutyne are described. By using an easily available base, a variety of vinyl ethers as well as sulfides are prepared at room temperature through two-phase nucleophilic addition reaction. Mechanistic study revealed that the stereoselectivity of vinyl ethers might depend on frontier orbital interaction under kinetic control.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.151693