Abstract The silver (II)-and manganese (III)-mediated radical reactions of 2-substituted-1, 4- naphthoquinones are described. Acyl radicals generated by the oxidative decarboxylation of α-keto acids with silver (I) nitrate and persulfate undergo efficient radical addition to the C= C bond of 2-(1-hydroxyalkyl)-1, 4-naphthoquinones and 2-(1-amidoalkyl)-1, 4- naphthoquinones. This reaction provides an effective method for the synthesis of naphtho ...