Synthesis of Pentafluorosulfanylated Ynamides and Further Functionalizations
Lucas Popek1, Gauthier Lefebvre2, Vincent Debrauwer1
1Université de Haute-Alsace, Université de Strasbourg, CNRS, LIMA, UMR 7042, 68000 Mulhouse, France.
Abstract:
Herein is described the first synthesis of SF5-ynamides, versatile building blocks featuring the pentafluorosulfanyl motif. This synthesis proceeds through a two-step sequence of radical SF5-addition onto the π-system of a wide range of terminal ynamides and derivatives substituted with various nitrogen fragments followed by a dehydrochlorination reaction. A selection of downstream functionalization reactions, including nucleophilic additions, cycloadditions, and sulfur ylide synthesis, highlights the wide-ranging applications of this novel type of functionalized SF5-building block.
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