Electrochemically Generated Copper(I)‐Catalyzed Click Chemistry: Triazole Synthesis and Insights into Their Photophysical Properties

Catalytic azide-alkyne cycloaddition via electrochemically generated cuprous species leading to 1,2,3-triazoles in good yield and regioselectivity was accomplished. Selected triazoles were applied for the spectrophotometric detection of transition metal analytes.

Abstract

Herein, we report the electro-click (e-CLICK) reaction via electrochemically generated copper(I) catalytic species. The reaction worked under constant potential electrolysis (−0.25 V) with copper(II) nitrate and 2,2′-bipyridine serving as pre-catalyst and ligand respectively. The reaction accommodates electronically different organic azides and terminal alkynes to afford 1,2,3-triazoles in good synthetic yields with excellent 1,4-regioselectivity. Compared to traditional click chemistry, the developed e-CLICK methodology avoids the use of external reducing agents such as sodium ascorbate. Absorptive properties of selected triazole products were assessed by UV-visible electronic spectra. Triazole (3 e) was further applied for the spectrophotometric detection of Co²⁺ and Cu²⁺ species.

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