Issue 21, 2023

Electrocatalytic oxidative C–H cycloamination towards tricyclic [1,2,4]triazolo-[3,4-i]purine nucleosides mediated by bromide ions

Abstract

An environmentally benign electrochemical approach is presented to access a diversely functionalized [1,2,4]triazolo[3,4-i]purine heterocyclic framework. A bromide-mediated indirect oxidation strategy was utilized to promote intramolecular C(sp2)–H cycloamination with high efficiency and under mild metal- and oxidant-free conditions. The method exhibits a broad substrate scope, which is well manifested by nucleoside substrates with one or even three hydroxy groups. A radical mechanism was proposed based on cyclic voltammetry and control experiments.

Graphical abstract: Electrocatalytic oxidative C–H cycloamination towards tricyclic [1,2,4]triazolo-[3,4-i]purine nucleosides mediated by bromide ions

Supplementary files

Article information

Article type
Research Article
Submitted
09 7 2023
Accepted
13 9 2023
First published
14 9 2023

Org. Chem. Front., 2023,10, 5369-5374

Electrocatalytic oxidative C–H cycloamination towards tricyclic [1,2,4]triazolo-[3,4-i]purine nucleosides mediated by bromide ions

Q. Yang, W. Li, Z. Zhang, H. Zhang, X. Li and H. Guo, Org. Chem. Front., 2023, 10, 5369 DOI: 10.1039/D3QO01050C

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