Iodine-catalyzed one-pot synthesis of unsymmetrical meso-substituted porphyrins

Benjamin Boëns (1) , Pierre-Antoine Faugeras (1) , Julien Vergnaud (1) , Romain Lucas (1) , Karine Teste (1) , Rachida Zerrouki (1)

1 LCSN - Laboratoire de Chimie des Substances Naturelles

The wide range use of 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin is well established, but its synthesis requires two steps and is not very practical. This article describes an iodine-catalyzed one-pot synthesis of this unsymmetrical porphyrin that uses commercial reagents and reactants as such, without prior distillation. Unsymmetrical mono functionalized porphyrins with various functional groups have also been obtained to validate this method. The influence of electronic effects of functional groups (donor or acceptor) has also been studied.

Domaines: Chimie; Chimie organique

Benjamin Boëns, Pierre-Antoine Faugeras, Julien Vergnaud, Romain Lucas, Karine Teste, et al.. Iodine-catalyzed one-pot synthesis of unsymmetrical meso-substituted porphyrins. Tetrahedron, 2010, 66 (11), pp.1994-1996. ⟨10.1016/j.tet.2010.01.055⟩. ⟨hal-00697387⟩