Acid-Promoted Amination of Cyclohexenone for the Divergent Synthesis of p-Aminophenols and Tertiary Amines

A tunable method for the selective preparation of p-aminophenol and tertiary amines from a secondary amine and cyclohexenone has been described. Nonaromatic cyclohexenones were used as an aryl source. The desired tertiary amine products were generated when using I₂ as the catalyst. This approach yields single-site-selective p-aminophenol without using I₂, and the ¹⁸O labeling experiments demonstrated that hydroxyl oxygen originates from O₂.