Regioselective C–H alkylation and alkenylation at the C5 position of 2-amino-1,4-naphthoquinones with maleimides under Rh(iii) catalysis

Abstract

Rhodium(III) catalyzed regioselective C–H alkylation and alkenylation at the C5 position of 1,4-naphthoquinone with maleimides under acidic and basic conditions, respectively, is described. The alkylamino substituents at the C2 position enabled the reaction to proceed efficiently. The alkylation reaction proceeds via a redox neutral Rh(III) pathway, whereas the alkenylation reaction takes place through the typical redox Rh(III) pathway to yield Rh(I) species.