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Synthesis 2009(4): 551-556  
DOI: 10.1055/s-0028-1083335
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reductive Amination - A Convenient Method for Generating Diverse, Mono-Functionalised 5,10,15,20-Tetraphenyl Porphyrins

Chris Welch, Stephen J. Archibald*, Ross W. Boyle*
Department of Chemistry, University of Hull, Kingston-upon-Hull, East Yorkshire, HU6 7RX, UK
Fax: +44(1482)466410; e-Mail: r.w.boyle@hull.ac.uk;
Further Information

Publication History

Received 11 August 2008
Publication Date:
27 January 2009 (online)

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Abstract

Formylation followed by reductive amination of 5,10,15,20-tetraphenyl porphyrin (TPP) is shown to be a versatile synthetic procedure for monosubstitution of the porphyrin core regiospecifically at one β-position. A diverse range of substituents can be introduced in this way in good yields, including cyclen aza-crown macrocycles.

Key words

porphyrin - substitution - cyclen - amination - regioselective

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