Synthesis of (Z)-fluoroallyl azides through aluminium-mediated defluorinative functionalization reactions. Issue 7 (11th February 2015)

• Record Type: Journal Article
• Authors: Sato, Azusa; Yanai, Hikaru; Suzuki, Daiki; Okada, Midori; Taguchi, Takeo
• Is Part Of: Tetrahedron letters. Volume 56:Issue 7(2015)
• Page Start: 925
• Page End: 929
• Publication Date: 2015-02-11
• Subjects: Fluoroalkene -- C–F bond cleavage -- Chlorination -- Azidation -- Aluminium reagents; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.12.128
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The reaction of difluorohomoallyl alcohols with Me2 AlCl in CH2 Cl2 selectively gave ( Z )-fluoroallyl chlorides via SN 2′ type defluorinative chlorination. These chlorides were easily converted to the corresponding ( Z )-fluoroallyl azides by the sequential nucleophilic azidation reaction using NaN3 . Direct defluorinative azidation of the difluorohomoallyl alcohols was also achieved by treating with Me3 SiN3 in the presence of Al(O i -Pr)3 . Fluoroallyl azides thus obtained successfully applied to the Huisgen 1, 3-dipolar cycloaddition chemistry.