Domino Ring‐Opening of N‐Tosyl Vinylaziridines Triggered by Aryne Diels‐Alder Reaction

The reactivity of N‐tosyl vinylaziridines toward arynes has been demonstrated under mild and transition‐metal‐free conditions to yield 2‐(phenanthren‐9‐yl)ethan‐1‐sulfamides in moderate to good yields. The selective synthesis of N‐H and N‐aryl products was accomplished using CsF in MeCN and KF/18‐C‐6 in 1,4‐dioxane, respectively. This cascade process involves a sequential Diels‐Alder reaction, ring‐opening aromatization, ene‐reaction, and selective N‐arylation reaction. magnified image