Acid-Promoted Amination\nof Cyclohexenone for the Divergent\nSynthesis of <i>p</i>‑Aminophenols and Tertiary Amines

A tunable method for the selective\npreparation of <i>p</i>-aminophenol and tertiary amines\nfrom a secondary amine and cyclohexenone\nhas been described. Nonaromatic cyclohexenones were used as an aryl\nsource. The desired tertiary amine products were generated when using\nI<sub>2</sub> as the catalyst. This approach yields single-site-selective <i>p</i>-aminophenol without using I<sub>2</sub>, and the <sup>18</sup>O labeling experiments demonstrated that hydroxyl oxygen\noriginates from O<sub>2</sub>.