A Novel Approach of Electrocatalytic Deamination from Aromatic Amide to Diarylimide on Ni-PTFE Modified Electrode

Wenjun Chen; Ziyang Huang; Hongyan Chen; Min Liu

doi:10.1002/chem.202400276

A Novel Approach of Electrocatalytic Deamination from Aromatic Amide to Diarylimide on Ni-PTFE Modified Electrode

Chemistry. 2024 May 16:e202400276. doi: 10.1002/chem.202400276. Online ahead of print.

Authors

Wenjun Chen¹, Ziyang Huang², Hongyan Chen³, Min Liu³

Affiliations

¹ Fujian Normal University, College of chemistry and materials science, Fuzhou, 350301, Fuzhou, CHINA.
² Fujian Normal University, College of Chemistry and Materials Science, Qishan Campus, No. 18 Wulongjiang Middle Avenue, Shangjie Town, 350117, Fuzhou, CHINA.
³ Fujian Normal University, College of chemistry and materials science, CHINA.

PMID: 38757422
DOI: 10.1002/chem.202400276

Abstract

A hydrophobic Ni-PTFE modified electrode has been prepared by constant current and cathodic electroplating with a nickel sheet as substrate in a PTFE suspension. Then the Ni-PTFE modified electrode was used for electroreduction from aromatic amide to diarylimide. The electrochemical characterizations such as cyclic voltammogram, EIS, polarization curves, and electrode stability have been carried out by electrochemical workstation. The structure of the electroreduction product diarylimide was characterized by 1HNMR, FT-IR, MS(Mass Spectrum), and EA(Elemental Analyzer). Based on the hydrophobicity of the electrode, an approach suggested that the phenyl ketone radical may be formed by electroreductive deamination at the cathode. With the construction of C-N bond by the radical coupling, the electrocatalytic reduction may be comprised of a one-electron process including an ECC (Electrochemical-Chemical-Chemical) process. The electroreduction of aromatic amide to diarylimide may be controlled by both charge migration and concentration polarization. Electrocatalytic reduction of aromatic amides on Ni-PTFE-modified electrodes is all well conversion ratio.

Keywords: Ni-PTFE modified electrode, electrocatalytic reduction, electrochemical deamination, diarylimide.