Vinyl nosylates as partner in copper and silver co-catalyzed Sonogashira cross-coupling reactions

Nicolas Cheval (1) , Barbara Hoffmann (1) , Anna Dikova (1) , Fatih Sirindil (1) , Philippe Bertus (2) , Aurélien Blanc (1) , Jean-Marc Weibel (1) , Patrick Pale (1)

1 Institut de Chimie de Strasbourg
2 IMMM - Institut des Molécules et Matériaux du Mans

Vinyl nosylates, readily obtained from β-dicarbonyl derivatives, could be efficiently engaged in Sonogashira cross-coupling reactions, either cocatalyzed by copper or silver salts. The para-nitrobenzenesulfonate (nosylate) group allows this coupling to be performed under very mild conditions (room temperature). These new leaving group and mild conditions could be applied to the synthesis of acetylenic coumarinyl derivatives and to the total synthesis of an acetylenic monoterpene natural product, named cleviolide.

Mots clés: Vinyl nosylates; Sonogashira; para-Nitrobenzenesulfonate; Cross-coupling; Palladium

Domaines: Chimie

Nicolas Cheval, Barbara Hoffmann, Anna Dikova, Fatih Sirindil, Philippe Bertus, et al.. Vinyl nosylates as partner in copper and silver co-catalyzed Sonogashira cross-coupling reactions. Tetrahedron, 2018, 74 (50), pp.7111-7119. ⟨10.1016/j.tet.2018.10.017⟩. ⟨hal-02312575⟩