A copper-catalysed cascade ester amidation/radical cyclization of 2-amino-1,4-naphthoquinones with α-bromocarboxylates to afford benzo[f]indole-2,4,9(3H)-triones is described, and the reaction has a broad substrate scope and the desired products are obtained in mostly moderate to good yields. Mechanism-probing experiments indicate that the otherwise challenging radical coupling reaction of α-bromocarboxylates with 2-amino-1,4-naphthoquinones is facilitated by a 5-endo radical cyclization.