Base-catalyzed stereoselective hydrophenoxylation and hydrothiolation of hexafluorobutyne. Issue 13 (26th March 2020)

• Record Type: Journal Article
• Authors: Bo, Zhao; Ji-Jun, Zeng; Sheng, Han; Dong-Huai, Tu; Jiang-Wei, Li; Wei, Zhang; Jian, Lu
• Is Part Of: Tetrahedron letters. Volume 61:Issue 13(2020)
• Publication Date: 2020-03-26
• Subjects: Base-catalyzed -- Nucleophilic addition -- Hydrophenoxylation -- Hydrothiolation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.151693
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Two-phase reaction. Mild reaction conditions. High Z selectivity. 100% Atom utilization. Abstract: 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.