title: Tri- and tetrasubstituted functionalized vinyl sulfides by radical allylation.
abstract: 2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition-elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates in highly stereoselective reactions with N-acylium cations leading to nitrogen-containing polycyclic structures.
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique , 91128 Palaiseau Cedex, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Debien
authors.forename: Marie-Gabrielle
authors.initials: MG
authors.lastname: Braun
authors.forename: Béatrice
authors.initials: B
authors.lastname: Quiclet-Sire
authors.forename: Samir Z
authors.initials: SZ
authors.lastname: Zard
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013440:Sulfides / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D005609:Free Radicals; D006845:Hydrocarbons, Fluorinated; D013440:Sulfides