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Paper | Special issue | Vol 93, No. 2, 2016, pp.483-511
Published online, 1st December, 2015
DOI: 10.3987/COM-15-S(T)20
Palladium-Catalyzed Cross-Coupling Reactions of Brominated Porphyrins with Functionalized Organomagnesium Reagents: Direct Preparation of Functional-Group-Bearing Free Base Porphyrins

Noriaki Sugita, Ikumi Tsuchiya, and Toshikatsu Takanami*

*Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

The direct preparation of free-base porphyrins possessing reactive functional groups such as esters, halides, amide, nitriles, and acetals is described. This method relies on a simple one-pot procedure that involves sequential palladium-catalyzed cross-coupling of brominated free-base porphyrins with functionalized aryl and alkenylmagnesium reagents, which are readily prepared by iodine–magnesium exchange of the corresponding organic iodides with the turbo Grignard reagent i-PrMgCl·LiCl, followed by demetallation of the resulting magnesium porphyrins under very mild conditions involving either a 1.2 M aqueous methanol solution of HCl or a 0.1 M methanol solution of citric acid at ambient temperature.