Palladium-Catalyzed Dearomative Arylvinylation Reaction of Indoles with N-Arylsulfonylhydrazones

A Pd-catalyzed dearomative arylvinylation reaction of indoles with N-arylsulfonylhydrazones as coupling partners is developed, which proceeds via a domino sequence involving dearomative carbopalladation, Pd-carbene migratory insertion, and regioselective β-hydride elimination. A range of 3-vinylindolines bearing vicinal quaternary and tertiary carbon stereocenters is achieved in moderate yields. The enantioselective reaction was established by using a chiral BINOL-based phosphoramidite ligand, which led to the arylvinylation products in good enantiomeric ratios and excellent diastereoselectivities.