Palladium-catalyzed -halogenations of acetanilides with -halosuccinimides via direct sp C-H bond activation in ball mills.

A solvent-free palladium-catalyzed -iodination of acetanilides using -iodosuccinimide as the iodine source has been developed under ball-milling conditions. This present method avoids the use of hazardous organic solvents, high reaction temperature, and long reaction time and provides a highly efficient methodology to realize the regioselective functionalization of acetanilides in yields up to 94% in a ball mill. Furthermore, the current methodology can be extended to the synthesis of -brominated and -chlorinated products in good yields by using the corresponding -halosuccinimides.