Cyclocarbopalladation: sequential cyclization and C-h activation/Stille cross-coupling in the Pd-5-exo-dig reaction.

A new cyclization and C-H activation/Stille cross-coupling reaction on a nonactivated aromatic has been discovered. The reaction is regioselective and controlled by the stannylated reagent. Labeling experiments have been performed that provide evidence for a complete transfer of the deuterium through the coordination sphere of palladium. [reaction: see text]