Scramble-Free Synthesis of Unhindered trans -A 2 B 2 -Mesoaryl Porphyrins via Bromophenyl Dipyrromethanes

-disubstituted porphyrins are highly valuable intermediates across diverse fields, but they pose a significant synthesis challenge in some cases due to scrambling and formation of complex mixtures. Conditions that minimize scrambling also lower yields, but steric hindrance around the meso-aryl subst...

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Published inOrganic letters Vol. 26; no. 8; pp. 1561 - 1565
Main Authors Alshammari, Muteb H, Alhunayhin, Sultanah M N, Hughes, David L, Chambrier, Isabelle, Cammidge, Andrew N
Format Journal Article
LanguageEnglish
Published United States 01.03.2024
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Summary:-disubstituted porphyrins are highly valuable intermediates across diverse fields, but they pose a significant synthesis challenge in some cases due to scrambling and formation of complex mixtures. Conditions that minimize scrambling also lower yields, but steric hindrance around the meso-aryl substituent can effectively suppress scrambling altogether. Here we report a straightforward approach to valuable trans-A B porphyrin intermediates that are otherwise very difficult to obtain, through use of removable blocking bromide substituents.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c04215