Scramble-Free Synthesis of Unhindered trans-A2B2‑Mesoaryl Porphyrins via Bromophenyl Dipyrromethanes

Trans-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...

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Veröffentlicht in:Organic letters 2024-03, Vol.26 (8), p.1561-1565
Hauptverfasser: Alshammari, Muteb H., Alhunayhin, Sultanah M. N., Hughes, David L., Chambrier, Isabelle, Cammidge, Andrew N.
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Sprache:eng
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Zusammenfassung:Trans-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-A2B2 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