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Acid and Solvent Effects on the Regioselectivity of Minisci-Type Addition to Quinolines Using Amino Acid Derived Redox Active Esters

Minisci-type reactions comprise an important class of reactions for the direct functionalization of basic heterocyclic compounds. On certain heterocycles, such as quinolines, Minisci-type reactions face a regioselectivity choice which often results in mixtures of regioisomers at the C2 and C4 positions, limiting utility. We present a study of the effect of solvent and Bronsted acid catalyst on regioselectivity in the addition of N-acetyl-substituted, α-amino alkyl radicals to quinolines. By tuning the solvent and acid combination we identify conditions that strongly favour C2 and strongly favour C4 and present a small scope of compatible substrates.