Direct Access to 2,3-Disubstituted Amido-Indenones through Annulation of 2-Iodobenzaldehydes with Ynamides

Stéphane Golling (1) , Pierre Hansjacob (1) , Nassim Bami (1) , Frédéric R Leroux (1, 2, 3, 4) , Morgan Donnard (1, 2, 3, 4)

1 LIMA - Laboratoire d'innovation moléculaire et applications
2 CNRS - Centre National de la Recherche Scientifique
3 UNISTRA - Université de Strasbourg
4 Université de Haute-Alsace (UHA) - Université de Haute-Alsace (UHA) Mulhouse - Colmar

In this paper we report the annulation reaction between 2-iodobenzaldehyde derivatives and various ynamides. This palladium-catalyzed reaction leads to rare polysubstituted amino-indenones in good yields with a regioselectivity up to complete. Remarkably, a regiodivergent selectivity has been identified between aryl and alkyl or silyl ynamides, with the first leading mainly to 2-amido-indenones and the second to 3-amido-indenones.

Domaines: Chimie organique; Catalyse

Stéphane Golling, Pierre Hansjacob, Nassim Bami, Frédéric R Leroux, Morgan Donnard. Direct Access to 2,3-Disubstituted Amido-Indenones through Annulation of 2-Iodobenzaldehydes with Ynamides. Journal of Organic Chemistry, 2022, ⟨10.1021/acs.joc.2c02054⟩. ⟨hal-03883448⟩