Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines

Abstract

Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is proposed for this transformation.