Iridium-catalyzed, ligand-controlled directed alkynylation and alkenylation of arenes with terminal alkynes†
We report iridium-catalyzed C–C formation between benzamides and terminal alkynes. With the choice of a suitable ligand, a C–H alkynylation or alkenylation product could be obtained selectively. The directed C–H alkynylation proceeded without the need for an external oxidant, while the directed C–H alkenylation likely involves an unusual vinylidene mechanism. This divergent reactivity provides access to both alkynylation and alkenylation products from the same set of starting materials.