Iodide assisted synthesis of amides on carbon electrode: application to N,N-diethylaminoethyl amide derivatives

Abstract

Amide bonds are highly prevalent in natural products and pharmaceuticals, making them one of the most important functional groups, such as N,N-diethylaminoethyl amide group commonly found in drugs. This study presents a novel electrochemical method for the direct condensation of carboxylic acids and amines, utilizing triphenylphosphine as a coupling agent and iodide as a redox mediator. A key innovation of this method is the use of low-cost graphite electrodes, which provide a scalable alternative to platinum- or boron-doped diamond (BDD) electrodes. Additionally, tetrabutylammonium iodide (TBAI) was employed as a more efficient mediator than the other iodide sources, achieving yields of up to 84%. The process was performed under mild conditions, with high functional group tolerance, and allowed for the synthesis of various amides, including N,N-diethylaminoethyl amide derivatives. This work demonstrates the potential of carbon electrodes and iodide for sustainable and efficient electrochemical amide synthesis with advantages in cost, scalability, and pharmaceutical applications.