The cross‐dehydrogenative‐coupling (CDC) reaction of benzoxazin‐2‐ones through visible‐light photoredox catalysis was developed. In the process of the reaction, an α‐amino radical intermediate is generated by using Ru(bpy)3Cl2 as a photoredox catalyst under visible‐light irradiation at room temperature. This intermediate is then oxidized, using O2 as terminal oxidant, to give an iminium ion intermediate. The iminium ion reacts directly with various aromatic nucleophiles to give the desired cross‐coupling products in yields of up to 80 %. This work provides a sustainable and environmentally friendly method for the synthesis of 3,4‐dihydro‐1,4‐benzoxazin‐2‐one derivatives.
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