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

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.

Regioselective Pyridine to Benzene Edit Inspired by Water-Displacement

“…Molecular edits involving nitrogen atoms have drawn particular attention of late, aimed at accelerating drug-discovery efforts given the prevalence of nitrogen heterocycles in FDA-approved drugs . Many elegant heterocycle interconversions have been reported which feature the insertion or deletion of a nitrogen atom, thereby exchanging hydrogen bond donors and acceptors while simultaneously shifting physicochemical properties like logD, polar surface area, solubility and p K a .…”