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Synthesis of meso -substituted porphyrins

Synthesis of meso -substituted porphyrins

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Synthesis of meso -substituted porphyrins

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  1. Synthesis of meso-substituted porphyrins Mariusz Tasior

  2. Rothemund method – in 1935... Rothemund, P., J. Am. Chem. Soc. 1935, 57, 2010.

  3. Rothemund method – in 1935... First report about effects of metals in pyrrole-aldehyde condensation: Ball, R. H. et al. J. Am. Chem. Soc. 1946, 68, 2278.

  4. Some general considerations...

  5. Some general considerations...

  6. Adler method Adler, A.D.; Longo, F. R.; Shergalis, W., J. Am. Chem. Soc. 1964, 86, 3145.

  7. Scope of Adler method

  8. Scope of Adler method

  9. Mixed-aldehyde condensation

  10. Mixed-aldehyde condensation Leznoff, C. C.; Svirskaya, P.I, Angew. Chem. In. Ed. 1978, 12, 947.

  11. Lindsey method 1979-... Lindsey, J. S., Hsu, H. C., Schreiman, I. C. Tetrahedron Lett. 1986, 27, 4969. Lindsey, J. S., Schreiman, I. C., Hsu, H. C., Kearney, P. C., Marguerettaz, A. M. Tetrahedron Lett. 1986, 27, 4969. Acid cocatalysis, salt effect: Lindsey et al. JPP, 2001, 5, 681

  12. Scope of Lindsey method

  13. Comparison of synthetic methods

  14. Routes to specific classes of meso-substituted porphyrins

  15. Trans-A2B2-porphyrins For dipyrromethane synthesis: Lindsey, J. S. et al. Org. Process Res. Dev. 2003, 7, 799. For condensation conidtions and scrambling: Lindsey, J. S. et al. J. Org. Chem. 1999, 8, 2864

  16. Scrambling

  17. Porphyrins bearing up to 4 different meso substituents

  18. Thank you...