Brønsted Acid Catalyzed Oxygenative Bimolecular Friedel–Crafts‐type Coupling of Ynamides

Abstract

Abstract A non‐metal approach for accessing α‐oxo carbene surrogates for a C−C bond‐forming bimolecular coupling between ynamides and nucleophilic arenes was developed. This acid‐catalyzed coupling features mild temperature, which is critical for the required temporal chemoselectivity among nucleophiles. The scope of nucleophiles includes indoles, pyrroles, anilines, phenols and silyl enolethers. Furthermore, a direct test of S N 2′ mechanism has been provided by employing chiral N,N′‐dioxides which also enlightens the nature of the intermediates in related metal‐catalyzed processes.