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.
Muñiz
Kilian
K
Institut de Chimie, UMR 7177, Université Louis Pasteur, 4 rue Blaise Pascal, F-67000 Strasbourg Cedex, France. muniz@chimie.u-strasbg.fr