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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TitreRegioselective C-H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation
Type de publicationJournal Article
Year of Publication2020
AuteursBousfiha A, Dime AKD, Mankou-Makaya A, Echaubard J, Berthelot M, Cattey H, Romieu A, Roger J, Devillers CH
JournalCHEMICAL COMMUNICATIONS
Volume56
Pagination884-887
Date PublishedJAN 18
Type of ArticleArticle
ISSN1359-7345
Résumé

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.

DOI10.1039/c9cc07351e