Tri- and tetrasubstituted functionalized vinyl sulfides by radical allylation
Laurent Debien1, Marie-Gabrielle Braun, Béatrice Quiclet-Sire
1Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique , 91128 Palaiseau Cedex, France.
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.
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