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Synfacts 2009(12): 1336-1336  
DOI: 10.1055/s-0029-1218189
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Tandem Heck Reaction/6π-Electrocyclization for the Synthesis of opp-Dibenzoporphyrins

Contributor(s): Timothy M. Swager, Rebecca R. Parkhurst
R. Deshpande, L. Jiang, G. Schmidt, J. Rakovan, X. Wang, K. Wheeler, H. Wang*
Miami University, Oxford, Oak Ridge National Laboratory and Eastern Illinois University, Charleston, USA
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Publikationsdatum:
20. November 2009 (online)

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Significance

Porphyrins fused to aromatic rings have many potential applications in material chemistry due to tunable and interesting photophysical and optoelectronic properties. The authors required an efficient route to benzoporphyrins for use in dye-sensitized solar cells. They designed a synthesis that exploits the known re­gioselective bromination of symmetrical tetrabenzoporphyrins to generate a substrate for Heck reaction with a variety of substituted alkenes. The Heck reaction was followed by in situ 6π-electrocyclization and aromatization to yield the desired benzoporphyrins.