Solid-State C-N Cross-Coupling Reactions with Carbazoles as Nitrogen Nucleophiles Using Mechanochemistry.

The palladium-catalyzed solid-state C-N cross-coupling of carbazoles with aryl halides via a high-temperature ball-milling technique has been reported. This reaction allowed simple, fast, and efficient synthesis of N-arylcarbazole derivatives in good to excellent yields without the use of large amounts of organic solvents in air. Importantly, the developed solid-state coupling approach enabled the cross-coupling of poorly soluble aryl halides with large polyaromatic structures that are barely reactive under conventional solution-based conditions.