The direct synthesis of N -(hetero)arylated heteroarenes has been realized via Cu-mediated C-N coupling of NH azaheterocycles with aryl C-H bonds under aerobic conditions. This protocol features a broad scope of both heterocyclic arenes (pyridine, quinoline, pyrazole, imidazole, furan, thiophene, benzofuran, and indole) and NH azaheterocycles (imidazole, pyrazole, indole, azindole, purine, indazole, benzimidazole, pyridone, carbazole), providing a versatile method for the synthesis of pharmaceutically important N -(hetero)arylated heteroarenes. The versatility of this reaction was further demonstrated by late-stage modification of marketed drugs, and by synthesis of a key intermediate for accessing a class of Angiotensin II receptor 1 antagonists.