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.

Automated summary

The study presents a palladium-catalyzed solid-state C-N cross-coupling of carbazoles with aryl halides via a high-temperature ball-milling technique, allowing for the efficient synthesis of N-arylcarbazole derivatives without the use of large amounts of organic solvents. Importantly, this method enables the coupling of poorly soluble aryl halides with large polyaromatic structures that are barely reactive under conventional solution-based conditions.