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 <i>via</i> 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 <i>N-</i>acylium cations leading to nitrogen-containing polycyclic structures