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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (10), p. 628-633, 2014

DOI: 10.3762/bjoc.10.54

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From porphyrin benzylphosphoramidate conjugates to the catalytic hydrogenation of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin

Journal article published in 2014 by Marcos C. de Souza, Leandro F. Pedrosa ORCID, Géssica S. Cazagrande, Vitor F. Ferreira ORCID, Maria G. P. M. S. Neves, José A. S. Cavaleiro ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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 (TPPF20) 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 TPPF20 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 TPCF20 and an ethanol/DMF/NEt3 mixture is more adequate to produce isobacteriochlorin (TPIF20).