Synthesis of 4-amino-7-oxyindoles <i>via</i> dearomatization of 4-alkyl-2-alkynylanilines and dual fragment incorporation with <i>O</i> -benzoylhydroxylamines

<i>O</i>-Benzoylhydroxylamines have been widely used as important amination reagents in C-N bond construction reactions; however, these reactions have exclusively focused on utilizing the amino group, with the benzoyloxy moiety often discarded as waste. Herein, we achieved the incorporation of both the NH₂ and benzoyloxy fragments of <i>O</i>-benzoylhydroxylamines into indole scaffolds <i>via</i> dearomatization of 4-alkyl-2-alkynylanilines and subsequent treatment with single-electron transfer (SET) reagents. The resulting 4-amino-7-oxyindoles allow for further selective structural modifications at the C-4 and C-7 positions as needed, facilitating drug screening investigations.