Non-ionic micelle-inspired electrochemical functionalization of diverse NH-heterocycles for the synthesis of β-aminoketones

Abstract

Alternatives to toxic organic solvents, transition metals, additives and bases are always desirable to reduce their environmental footprint, are they are now being reevaluated by developing more sustainable electrolyte-free electro-organic synthesis. Here, we utilized the biodegradable and economical aqueous micelle polysorbate 20 as both solvent and electrolyte for the aza-Michael addition reaction. This atom-economical and regioselective methodology, with a broad substrate scope, enables the functionalization of 16 different heterocycles for the synthesis of highly valued heterocyclic β-aminoketones in moderate to excellent yields. Preliminary mechanistic studies suggested the involvement of N-centered and C-centered radical intermediates in the electrochemical process. This approach paves the way for more sustainable and green electrochemical methodologies in organic synthesis.