ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Robby Gus Mahardika, Ade Danova, Elvira Hermawati, and Anita Alni

Organic Chemistry Division, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Bandung, Indonesia

E-mail: alni@itb.ac.id

Received: 10 January 2025  Accepted: 6 May 2025

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.

Keywords: Chemical modification; Chemical Synthesis; Electrochemistry; Electrocatalysis; Industrial Chemistry; Organocatalysis; Electrosynthesis; Graphite electrode; Electrocatalysis; Amidation; Amide

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-025-04120-6

Chemical Papers 79 (8) 5219–5236 (2025)