An efficient one-flask synthesis of N-confused tetraphenylporphyrin |
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Authors: | Geier G R Haynes D M Lindsey J S |
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Institution: | Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA. |
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Abstract: | formula: see text] N-Confused meso-substituted porphyrin is a porphyrin isomer previously available from one-flask porphyrin syntheses as a low-yield byproduct (< 7.5%). We have found that methanesulfonic acid catalyzed condensation of pyrrole and benzaldehyde followed by DDQ oxidation provides N-confused tetraphenylporphyrin (NC-TPP) in up to 39% yield in analytical scale experiments. Preparative synthesis provided an isolated yield of 35% (800 mg). This represents a > 5-fold yield improvement and makes significant quantities of NC-TPP readily available. |
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