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 iyl 2023
Accepted
13 sen 2023
First published
14 sen 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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