Tri- and Tetra-Substituted Functionalized Vinyl Sulfides by Radical Allylation

Laurent Debien (1) , Marie-Gabrielle Braun (1) , Beatrice Quiclet-Sire (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

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.

Domaines: Chimie organique

Laurent Debien, Marie-Gabrielle Braun, Beatrice Quiclet-Sire, Samir Z. Zard. Tri- and Tetra-Substituted Functionalized Vinyl Sulfides by Radical Allylation. Organic Letters, 2013, 15 (24), pp.6250-6253. ⟨10.1021/ol403103u⟩. ⟨hal-00967569⟩