Abstract
AbstractThe 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[2,3‐c]furan‐4,9‐diones and benzo[f]isoindole‐4,9‐diones. In the presence of O2, manganese(III) acetate oxidation of β‐keto esters also generates acyl radicals, which then undergo radical addition to 2‐(1‐amidoalkyl)‐1,4‐naphthoquinones, and subsequently, benzo[f]isoindole‐4,9‐diones are produced.
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