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 I 2 as the catalyst. This approach yields single-site-selective p -aminophenol without using I 2 , and the 18 O labeling experiments demonstrated that hydroxyl oxygen originates from O 2 .