On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins

Abstract : The synthesis of functionalized porphyrins and their conjugates from meso-tetraarylporphyrins through the acylation and the oxidation of beta-aminoporphyrins was investigated. 2,3-Dioxochlorins were prepared by the oxidation of a variety of beta-aminoporphyrins and subsequently used in a condensation reaction with functionalized aromatic aldehydes and ammonium acetate to form beta-functionalized porphyrins bearing a fused imidazole ring. Under optimized experimental conditions both reactions tolerate various functional groups and afford the products in an appropriate overall yield. The mildness and usefulness of this methodology are illustrated by several examples including the synthesis of porphyrins bearing receptor groups and water-solubilizing moieties.
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01427448
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : jeudi 5 janvier 2017 - 16:50:36
Dernière modification le : jeudi 4 avril 2019 - 10:18:05

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Inna A. Abdulaeva, Kirill P. Birin, Julien Michalak, Anthony Romieu, Christine Stern, et al.. On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins. New Journal of Chemistry, Royal Society of Chemistry, 2016, 40 (7), pp.5758 - 5774. ⟨http://pubs.rsc.org/en/content/articlelanding/2016/nj/c5nj03247d#!divAbstract⟩. ⟨10.1039/c5nj03247d⟩. ⟨hal-01427448⟩

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