Tri- and Tetra-Substituted 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.
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Submitted on : Saturday, March 29, 2014 - 11:36:49 AM
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Laurent Debien, Marie-Gabrielle Braun, Beatrice Quiclet-Sire, Samir Z. Zard. Tri- and Tetra-Substituted Functionalized Vinyl Sulfides by Radical Allylation. Organic Letters, American Chemical Society, 2013, 15 (24), pp.6250-6253. ⟨10.1021/ol403103u⟩. ⟨hal-00967569⟩

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