Copper-Catalyzed C–N Coupling Reactions of Nitrogen-Rich Compounds – Reaction of Iodofurazans with s-Tetrazinylamines

Access to unsymmetrical secondary dihetarylamines through the Cu(OAc)2/2-acetylcyclohexanone catalyzed cross-coupling of s-tetrazinylamines with iodofurazans has been developed. The reaction displays good functional group tolerance, involving nitro, azido, and azo groups, which are critical for the construction of energetic materials. Both 3,6-disubstituted and annelated s-tetrazines react readily with iodofurazans to furnish the desired products.