Advancing Palladium-Catalyzed C−N Bond Formation: Bisindoline Construction from Successive Amide Transfer to Internal Alkenes

The sequential transfer of two sulfonamides to internal alkenes affords the construction of vicinal diamines. In the presence of a palladium catalyst, the reaction proceeds through two mechanistically different C-N bond formation reactions. It is initiated by aminopalladation, followed by a reductive amination of a palladated secondary carbon. The overall process proceeds with complete selectivity for both steps and thereby generates a convenient access to heterocyclic structures such as bisindolines, annelated indolines, and bispyrrolidines.