Issue 24, 2019

Proton-coupled electron transfer oxidation of O–H bond by the N-radical cation of Wurster's blue salt (TMPDA˙+)

Abstract

Here, we report the proton-coupled electron transfer reaction between TEMPO-H and Wurster's blue salt (TMPDA˙+). TMPDA˙+ could abstract a hydrogen atom from 2,2,6,6-tetramethyl-1-hydroxy-piperidine (TEMPO-H) via concerted electron–proton transfer and displayed a large KIE (7.05 ± 0.07 at 298 K). This work shows that a nitrogen-centered radical cation (R3+) such as TMPDA˙+ is more than a weak single-electron oxidant, and can also be an effective PCET reagent for oxidative bond activation.

Graphical abstract: Proton-coupled electron transfer oxidation of O–H bond by the N-radical cation of Wurster's blue salt (TMPDA˙+)

Supplementary files

Article information

Article type
Communication
Submitted
15 saus. 2019
Accepted
25 vas. 2019
First published
25 vas. 2019

Chem. Commun., 2019,55, 3465-3468

Proton-coupled electron transfer oxidation of O–H bond by the N-radical cation of Wurster's blue salt (TMPDA˙+)

H. Li, Y. Guo, J. Wu and M. Zhang, Chem. Commun., 2019, 55, 3465 DOI: 10.1039/C9CC00354A

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