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

Abstract

In this work, a novel C(sp3)–C(sp2) 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.

Keywords

• ball mill
• benzoxazinones
• cdc reactions
• heterocycles