Palladium-catalyzed synthesis of carbazoles from N-(2-halophenyl)-2,6-diisopropylanilines via C–C cleavage

The synthesis of 1-isopropyl-substituted carbazoles by the palladium-catalyzed dealkylative cyclization of N-(2-halophenyl)-2,6-diisopropylanilines is described. The reaction involves intramolecular C–C bond formation, coupled with the cleavage of a C–X bond and a C–C bond, and is proposed to proceed through the formation of a dearomatized intermediate.