Work

Electrochemical heteroarylation and amidation of alkanes using activated glassy carbon electrodes without mediators

Year: 2025

Type: article

Abstract: The functionalization of challenging unactivated C(sp3)–H bonds was achieved electrocatalytically via hydrogen atom transfer and without mediators. This was possible through the sole activation of the surface of the Glassy Carbon Electrode (GCE) in an electrochemical fashion using a phosphate buffer. This activation produced oxygenated functional groups on the surface, capable of abstracting these hydrogen atoms from C(sp3)–H of alkanes. Minisci and Ritter-type reactions were achieved using this procedure. Extensive characterization of the activated GCE (AGCE) and preliminary mechanistic studies allow us to propose plausible reaction mechanisms. Furthermore, a regular battery can be used within this protocol to achieve the desired substituted alkanes under inexpensive and user-friendly conditions. Aliphatic compounds play a crucial role in pharmaceutical and agrochemical industries, however, the selective modification of these structures remains challenging due to the high strength of unactivated C(sp3)–H bonds. Here, the authors report a Minisci-type alkylation of azaarenes with alkanes and a Ritter reaction between alkanes and nitriles using an activated glassy carbon electrode, achieving electrocatalytic functionalization of inert alkanes that eliminates the need for traditional mediators or metals.

Source: Communications Chemistry

DOI: 10.1038/s42004-025-01494-2

Authors: Loris Laze, Jose C. Gonzalez-Gomez, Irene Bosque

Institution: University of Alicante

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Affordable and clean energy

Open Access status: gold

Estimated APC paid: $3,690