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

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.

SUBMITTER: Alshammari MH 

PROVIDER: S-EPMC10913071 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Scramble-Free Synthesis of Unhindered <i>trans</i>-A<sub>2</sub>B<sub>2</sub>-Mesoaryl Porphyrins via Bromophenyl Dipyrromethanes.

Alshammari Muteb H MH   Alhunayhin Sultanah M N SMN   Hughes David L DL   Chambrier Isabelle I   Cammidge Andrew N AN  

Organic letters 20240219 8

<i>Trans</i>-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<sub>2</sub>B<sub>2</sub> porphyrin intermediates that are otherwise ver  ...[more]