Issue 7, 2016

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 β-aminoporphyrins was investigated. 2,3-Dioxochlorins were prepared by the oxidation of a variety of β-aminoporphyrins and subsequently used in a condensation reaction with functionalized aromatic aldehydes and ammonium acetate to form β-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.

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

Supplementary files

Article information

Article type
Paper
Submitted
17 Nov 2015
Accepted
03 Feb 2016
First published
04 Feb 2016

New J. Chem., 2016,40, 5758-5774

Author version available

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

I. A. Abdulaeva, K. P. Birin, J. Michalak, A. Romieu, C. Stern, A. Bessmertnykh-Lemeune, R. Guilard, Y. G. Gorbunova and A. Yu. Tsivadze, New J. Chem., 2016, 40, 5758 DOI: 10.1039/C5NJ03247D

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