Direct Synthesis of 2‑Functionalized 3‑Nitroindoles from Diazo(nitro)acetanilides

2-Hydroxyl/acetoxy-3-nitroindoles are directly and efficiently prepared in good to excellent yields from diazo(nitro)acetanilides under the catalysis of Cu(MeCN)4PF6 in DCM through an intramolecular aromatic C–H insertion or followed by acetylation. 2-Hydroxyl-3-nitroindoles can be further transformed to 3-halo-3-nitroindolin-2-ones and 3-alkanamidoindolin-2-ones readily. All of them are important synthetic building blocks for construction of indole derivatives.