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In this work, a novel C(sp 3 )–C(sp 2 ) cross-dehydrogenative-coupling method is developed to react benzoxazin-2-one derivatives with various indoles. As a result, combined use of ball milling and Fe( ii ) catalysis leads to rapid coupling of 1,4-benzoxazinones with derivatives of indole. Under the conditions, derivatives of  1  couple with various indoles at room temperature to produce good yields of the desired compounds within 0.5–2 h time period. Thus, derivatives of both starting materials couple smoothly under relatively mild conditions to give good yields of  3 .

Synergistic promoting effect of ball milling and Fe( ii ) catalysis for cross-dehydrogenative-coupling of 1,4-benzoxazinones with indoles