Synthesis of Triazoles by Electro-Assisted Click Reaction Using a Copper Foil Electrode

Journal of the Brazilian Chemical Society

article

Carre-Rangel, Luceldi¹  Espinoza, Karla A.¹  Oropeza-Guzmán, Mercedes T.¹  Rivero, Ignacio A.¹ 

[1] Instituto Tecnológico de Tijuana

关键词: click reaction;    azide;    triazole;    Cu electrooxidation;    organic electrosynthesis;   

DOI  :  10.21577/0103-5053.20210035

学科分类：内科医学

来源: SciELO

【 摘 要 】

This paper presents an innovative pathway for the synthesis of triazoles using the well-known “click chemistry” assisted by the electrochemical oxidation of metallic Cu 0 . The click reaction is used to couple a wide range of biological interest compounds. In this case, faster and less polluting methods for a biological environment was achived by in situ Cu 0 electrooxidation, providing the suitable quantity of catalyst required by click reaction. The electrochemical cell was composed of a copper foil as the working electrode, a platinum wire serving as a counter electrode, and an Ag/AgCl wire as the reference electrode. Linear anodic sweep voltammetry in a tert -butanol-water medium (1:1), an electrolyte of tetrabutylammonium tetrafluoroborate (TBATFB), showed the onset potential of Cu 0 electrooxidation. Using the same electrode configuration three different triazoles were prepared under constant electrode potential, in a short time (60 min), and splendid yields (78-90%). These results indicate that the in situ Cu I formation occurs on the surface of the copper foil. A pulse potential program has also been implemented in which a yield of 92% was achieved, reducing electrode passivation and consequently increasing the process efficiency. The electro-assisted click reactions are highly efficient to produce triazoles by an innovative electrochemical reaction. The products were characterized by infrared (IR), nuclear magnetic resonance ( 1 H and 13 C NMR), and mass spectrometry (MS).

【 授权许可】

CC BY