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

Abstract

Alternatives to toxic organic solvents, transition metal, additives and bases are always desirable to reduce its environmental footprint, are now being re-evaluated by developing more sustainable electrolyte free electro-organic synthesis. Here, we utilized biodegradable and economical aqueous micelle polysorbate 20 as both solvent and electrolyte for 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 electrochemical process. This approach paves the way for more sustainable and green electrochemical methodologies in organic synthesis.