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Regioselective halogenation and palladium-catalysed couplings on 5,15-diphenylporphyrin

SAKTHI SHANMUGATHASAN

Department of Biological Sciences, University of Essex, Wivenhoe Park, Colchester, Essex CO4 3SQ, UK

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CLAIRE K. JOHNSON

Department of Chemistry, University of British Columbia, Vancouver, BC, Canada

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CHRISTINE EDWARDS

Department of Biological Sciences, University of Essex, Wivenhoe Park, Colchester, Essex CO4 3SQ, UK

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E. KEITH MATTHEWS

Department of Pharmacology, University of Cambridge, Tennis Court Road, Cambridge CB2 1QJ, UK

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DAVID DOLPHIN

Department of Chemistry, University of British Columbia, Vancouver, BC, Canada

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, and

ROSS W. BOYLE

Department of Biological Sciences, University of Essex, Wivenhoe Park, Colchester, Essex CO4 3SQ, UK

Corresponding author: Department of Biological Sciences, University of Essex, Wivenhoe Park, Colchester, Essex CO4 3SQ, UK.

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https://doi.org/10.1002/(SICI)1099-1409(200004/05)4:3<228::AID-JPP199>3.0.CO;2-7Cited by:55 (Source: Crossref)

Abstract

5,15-Diphenylporphyrin was regiospecifically halogenated in high yield to give 5-iodo-15-bromo-10,20-diphenylporphyrin, which was then subjected to Heck and Stille-type coupling reactions to form unsymmetrically substituted porphyrins. The regioselectivity of the iodination of diphenylporphyrins and subsequent formation of amphiphilic porphyrins via palladium-based methodology was also studied. The utility of this method for the synthesis of photodynamic sensitisers has been demonstrated on AR4-2J rat pancreatic carcinoma cells.

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