Regiodivergent cascade cyclization/alkoxylation of allenamides via N-protecting group driven rearrangement to access indole and indoline derivatives

A mild, palladium-catalyzed domino Heck-cyclization/alkoxylation sequence of aryl halide tethered allenamides is described, providing regiodivergent indole and indoline derivatives controlled by the N-protecting group. This room temperature reaction provided a functionalizable olefinic moiety with broad substrate scope. Preliminary mechanistic studies support the rearrangement of an indoline-derived intermediate to indoles with the N -acetyl allenamides forming free (NH) indoles.