Synthesis of Aromatic N-Oxides Using Electrochemically Generated Peroxodicarbonate

Org Lett. 2024 Mar 1;26(8):1607-1611. doi: 10.1021/acs.orglett.3c04386. Epub 2024 Feb 16.

Abstract

Electrochemically generated green platform oxidizers like peroxodicarbonate (PODIC) constitute a game-changing technology in terms of sustainable chemistry while serving as an alternative counterreaction in the electrochemical hydrogen evolution. Peroxodicarbonate avoids the storage and shipping of concentrated hydrogen peroxide solution. We herein disclose an efficient method for the N-oxidation of quinolines, pyridines, and complex tertiary amines. The use of phenoyloxy succinimide (POSI) is the decisive factor for obtaining N-oxides (28 examples) in isolated yields of up to 98%.