FeIII/TBHP mediated remote C–O bond construction of 8-aminoquinolines: access to methoxylation and cyanomethoxylation

Abstract

Novel approaches to C5 selective methoxylation and cyanomethoxylation of 8-aminoquinolines under the Fe^III/TBHP system were developed. Various substituted quinolines were tolerated to afford the corresponding ether products. A plausible mechanism was proposed involving the addition of alkoxyl radicals to an iron-chelated intermediate. In these protocols, TBHP acted as not only a radical initiator, more importantly, but also an “oxygen” source involved in the ether bond formation, which was investigated successfully for the first time.