Exploring N-centered umpolung reactivity in photoredox-catalyzed amidation with an α-iminoester

Abstract

The synthesis of amides and their derivatives has gained significant attention from the scientific community in recent decades due to the presence of amide moieties in many bioactive organic molecules. Pursuing sustainable chemistry using cost-effective starting materials under mild reaction conditions is intriguing and challenging. In this context, we present a method for the direct synthesis of amides from α-keto acids and α-iminoesters. This approach employs an Ir-based photocatalyst to enable redox-neutral C–N bond formation at room temperature through N-center umpolung chemistry. This straightforward protocol is compatible with a broad range of functional groups, allowing for the efficient production of amides from aromatic keto acids and imines as coupling partners in an atom-economical manner.