Iridium-catalyzed double incorporation reaction of N-benzylmaleimide to styrene via ortho-C–H bond activation, initiated by precoordination of the double bond of styrene to iridium

Reaction of styrene with N-benzylmaleimide in the presence of [IrCl(cod)]2 (5 mol %) and bpy (10 mol %) in an autoclave (1 MPa of Ar) at 150 °C for 18 h stereoselectively led to the formation of a new cyclic product. The structure of the product suggests that a novel iridium-catalyzed double incorporation reaction takes place via a metallacyclopentane formed after ortho-C–H activation.