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Efficient synthesis of free-base 2-formyl-5,10,15,20-tetraarylporphyrins, their reduction and conversion to [(porphyrin-2-yl)methyl]phosphonium salts

Bonfantini, Edia E; Burrell, Anthony K; Campbell, Wayne M; Crossley, Maxwell; Gosper, Jeffrey J; Harding, Margaret; Officer, David L; Reid, David C W


A highly efficient synthesis of 2-formyl-5,10,15,20-tetraarylporphyrins, 1 and 2, that can be carried out on multi-gram scales is reported. The key steps in the sequence involve use of copper(II) chelation to ensure very efficient electrophilic substitution, and the demetalation of the intermediate iminium salt that results from Vilsmeier-Haack formylation of the copper(II) porphyrins prior to base-catalyzed hydrolysis of the salt to the corresponding free-base 2-formylporphyrin. This sequence...[Show more]

CollectionsANU Research Publications
Date published: 2002
Type: Journal article
Source: Journal of Porphyrins and Phthalocyanines
DOI: 10.1142/s108842460200083x


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