An electrochemical oxidative multicomponent cascade annulation of ketones and amines used to produce imidazoles

Abstract

An electrochemical dehydrogenative [2 + 2 + 1] annulation used for the synthesis of imidazoles has been developed under undivided electrolytic conditions.

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

“…He and co‐workers [44] reported a mechanistically very similar iodide mediated electrochemical dehydrogenative annulation reaction to Scheme 32. The substrate scope of this methodology was, therefore, broader in this case, and typical aryl ketones like 2‐acetylfuran and 1,2‐diphenylethanone reacted smoothly to afford the desired product in good yields (Scheme 33).…”

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

“…Imidazoles could also be synthesized via an electrochemical procedure by Zeng, Li et al 210 To achieve the formation of this heterocyclic scaffold, aryl ketones and amines were employed in a multicomponent fashion. Despite not favoring aliphatic ketones, many functionalities were tolerated, including heterocyclic structures, alkenyl and alkynyl bearing amines, and the methyl ester of glycine as well (Scheme 111).…”

Recent advances in the electrochemical reactions of nitrogen-containing organic compounds

“…An electrochemical transition metal and peroxide-free oxidative multicomponent cascade dehydrogenative [2 + 2 + 1] annulations of ketones and amines for the synthesis of imidazoles were reported by He et al 17 The reaction proceeded via the formation of α-iodo ketone from the reaction of aryl methyl ketone with iodine, followed by nucleophilic attack of the amine to the C–I bond to form α-amino ketone. Finally, condensation of the α-amino ketone with benzylamine, cyclization, and aromatization via an oxidative dehydrogenation reaction gave product 4 ( Scheme 5 ).…”