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

Authors :
Alshammari MH
Alhunayhin SMN
Hughes DL
Chambrier I
Cammidge AN
Source :
Organic letters [Org Lett] 2024 Mar 01; Vol. 26 (8), pp. 1561-1565. Date of Electronic Publication: 2024 Feb 19.
Publication Year :
2024

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-A <subscript>2</subscript> B <subscript>2</subscript> porphyrin intermediates that are otherwise very difficult to obtain, through use of removable blocking bromide substituents.

Details

Language :
English
ISSN :
1523-7052
Volume :
26
Issue :
8
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
38373336
Full Text :
https://doi.org/10.1021/acs.orglett.3c04215