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

TitleRegioselective halogenation and palladium-catalysed couplings on 5,15-diphenylporphyrin
Publication TypeJournal Article
Year of Publication2000
AuthorsShanmugathasan, S, Johnson, CK, Edwards, C, Matthews, EK, Dolphin, D, Boyle, RW
JournalJournal of Porphyrins and Phthalocyanines
Volume4
Pagination228-232
Date PublishedApr-May
Type of ArticleArticle
ISBN Number1088-4246
KeywordsALKYNYLATION, amphiphiles, CROSS-COUPLING, IODINATION, palladium, PHOTODYNAMIC THERAPY, porphyrins
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. Copyright (C) 2000 John Wiley & Sons, Ltd.

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