Oxidative C–N fusion of pyridinyl-substituted porphyrins

Mathieu Berthelot; Guillaume Hoffmann; Asmae Bousfiha; Julie Echaubard; Julien Roger; Hélène Cattey; Anthony Romieu; Dominique Lucas; Paul Fleurat-Lessard; Charles H. Devillers

doi:10.1039/C8CC01375F

Oxidative C–N fusion of pyridinyl-substituted porphyrins†

Mathieu Berthelot,^a Guillaume Hoffmann,

^a Asmae Bousfiha,^a Julie Echaubard,^a Julien Roger,

^a Hélène Cattey,

^a Anthony Romieu,

^ab Dominique Lucas,

^a Paul Fleurat-Lessard

^a and Charles H. Devillers

*^a

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* Corresponding authors

^a Institut de Chimie Moléculaire de l’Université de Bourgogne UMR6302, Université de Bourgogne Franche-Comté, 9 avenue Alain Savary, Dijon 21078, France
E-mail: charles.devillers@u-bourgogne.fr

^b Institut Universitaire de France, 1, Rue Descartes, Bâtiment MONGE, 75231 Paris, France

Abstract

The mild (electro)chemical oxidation of pyridin-2-ylthio-meso substituted Ni(II) porphyrins affords C–N fused cationic and dicationic pyridinium-based derivatives. These porphyrins are fully characterized and the molecular structure of one of them was confirmed by X-ray crystallography. A mechanism for the intramolecular oxidative C–N coupling is proposed based on theoretical calculations and cyclic voltammetry analyses.

Chemical Communications

Oxidative C–N fusion of pyridinyl-substituted porphyrins†

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