Scramble-free synthesis of unhindered trans-A2B2-mesoaryl porphyrins via bromophenyl dipyrromethanes

Alshammari, Muteb H., Alhunayhin, Sultanah M. N., Hughes, David L., Chambrier, Isabelle and Cammidge, Andrew N. ORCID: https://orcid.org/0000-0001-7912-4310 (2024) Scramble-free synthesis of unhindered trans-A2B2-mesoaryl porphyrins via bromophenyl dipyrromethanes. Organic Letters, 26 (8). pp. 1561-1565. ISSN 1523-7060

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Abstract

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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry (former - to 2024)
Faculty of Science > School of Biological Sciences
Depositing User: LivePure Connector
Date Deposited: 08 Apr 2024 09:30
Last Modified: 19 Dec 2024 01:12
URI: https://ueaeprints.uea.ac.uk/id/eprint/94851
DOI: 10.1021/acs.orglett.3c04215

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