6533b85bfe1ef96bd12ba9eb

RESEARCH PRODUCT

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

Abdou K. D. DimeJulie EchaubardAsmae BousfihaJulien RogerAmelle Mankou-makayaMathieu BerthelotHélène CatteyCharles H. DevillersAnthony Romieu

subject

Protonation010402 general chemistry01 natural sciencesCatalysischemistry.chemical_compound[CHIM.ANAL]Chemical Sciences/Analytical chemistryPyridinePolymer chemistryMaterials ChemistryNucleophilic substitution[CHIM.COOR]Chemical Sciences/Coordination chemistryAmination[CHIM.ORGA]Chemical Sciences/Organic chemistry010405 organic chemistryMetals and AlloysFree base[CHIM.MATE]Chemical Sciences/Material chemistryGeneral ChemistryPorphyrin0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialschemistryCeramics and CompositesPyridiniumPiperidine

description

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.

https://doi.org/10.1039/c9cc07351e