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Synfacts 2008(12): 1276-1276  
DOI: 10.1055/s-0028-1087303
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Anthracene-Fused Porphyrins

Contributor(s): Timothy M. Swager, Rebecca R. Parkhurst
N. K. S. Davis, M. Pawlicki, H. L. Anderson*
University of Oxford, UK
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

The authors synthesized the first examples of anthracene-fused porphyrins (2c, 4) via a Suzuki coupling followed by oxidative fusion. Attempts at oxidative fusion were only successful with electron-rich meso-(9-anthryl)porphyrin ­derivatives, which is consistent with results using pyrene. Regioselective synthesis of 10-bromo-1,8-dialkoxyanthracene also provided a challenge which the authors were able to circumvent through the use of 1,8-diacetoxyanthracene and subsequent deprotection.