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The Synthesis of Meso-Substituted Porphyrins

  • Chapter
Metalloporphyrins Catalyzed Oxidations

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 17))

Abstract

The synthesis of meso-substituted porphyrins has traditionally been achieved under rather forcing conditions (Figure 1). In the Rothemund method (ca. 1941) an aldehyde and pyrrole are reacted in pyridine in a sealed tube at 220°C for 48 hours [1]. This approach gives tetraphenylporphyrin in 9% yield but has quite limited scope. In the Adler method (ca. 1964) an aldehyde and pyrrole are reacted in refluxing propionic acid (141°C) for 30 min in an open beaker, followed by isolation of the porphyrin crystals upon cooling [2–5]. The Adler method affords ~20% yields, is easy to implement, and has made possible the synthesis of an impressive number of meso-substituted porphyrins.

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  1. Department of Chemistry, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, PA, 15213, USA

    Jonathan S. Lindsey

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  1. University of Milan, Italy

    Fernando Montanari

  2. University of Pavia, Italy

    Luigi Casella

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Lindsey, J.S. (1994). The Synthesis of Meso-Substituted Porphyrins. In: Montanari, F., Casella, L. (eds) Metalloporphyrins Catalyzed Oxidations. Catalysis by Metal Complexes, vol 17. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-2247-6_2

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