N-Oxide-to-Carbon Transmutations of Azaarene N-Oxides

Org Lett. 2024 May 24;26(20):4280-4285. doi: 10.1021/acs.orglett.4c01263. Epub 2024 May 13.

Abstract

Reactions that change the identity of an atom within a ring system are emerging as valuable tools for the site-selective editing of molecular structures. Herein, we describe the expansion of an underdeveloped transformation that directly converts azaarene-derived N-oxides to all-carbon arenes. This ring transmutation exhibits good functional group tolerance and replaces the N-oxide moiety with either unsubstituted, substituted, or isotopically labeled carbon atoms in a single laboratory operation.