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Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation

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Abstract

Four free base aminoporphyrins were synthesized in two steps via regioselective anodic nucleophilic substitution with pyridine followed by ring opening of the electrogenerated pyridinium with piperidine. The X-ray crystallographic structure of the unstable 2-aminotetraphenylporphyrin was solved. Protonation of this latter compound leads to the stable diiminium porphyrin salt.

Graphical abstract: Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation

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Article information


Submitted
18 Sep 2019
Accepted
12 Dec 2019
First published
12 Dec 2019

Chem. Commun., 2020, Advance Article
Article type
Communication

Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation

A. Bousfiha, A. K. D. Dimé, A. Mankou-Makaya, J. Echaubard, M. Berthelot, H. Cattey, A. Romieu, J. Roger and C. H. Devillers, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC07351E

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