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From Porphyrin Benzylphosphoramidate Conjugates to the Catalytic Hydrogenation of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin

From Porphyrin Benzylphosphoramidate Conjugates to the Catalytic Hydrogenation of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin

Marcos C de Souza, Leandro F Pedrosa, Géssica S Cazagrande, Vitor F Ferreira, Maria G P M S Neves, José A S Cavaleiro

Beilstein J Org Chem. 2014 Mar 10;10:628-33.

PMID: 24778713

Abstract:

Three new porphyrin aminoalkyl dibenzylphosphoramidates were synthesized by nucleophilic aromatic substitution of one p-fluorine atom of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPPF 20 ) by primary aminoalkyl dibenzylphosphoramidates. The nucleophilic aromatic substitution was promoted by microwave irradiation in N-methyl-2-pyrrolidinone. Attempts to remove the benzyl groups of the phosphoramidate moiety by hydrogenolysis with 10% Pd/C led to the cleavage of the P-N bond and the reduction of the macrocycle to hydroporphyrin-type derivatives. The extent of the effect of the catalytic hydrogenation to TPPF 20 with 10% Pd/C was then studied with a variety of solvents. The results showed that ethanol/DMF is the solvent of choice to produce chlorin TPCF 20 and an ethanol/DMF/NEt3 mixture is more adequate to produce isobacteriochlorin (TPIF 20 ).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP25440146-B	5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin		25440-14-6	Price

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