Synthesis of meso -substituted porphyrins

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

16. 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

17. Scrambling

18. Porphyrins bearing up to 4 different meso substituents

20. Thank you...