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Stepwise Preparation of meso ‐Tetraphenyl‐ and meso ‐Tetrakis(4‐trifluoromethylphenyl)bacteriodilactones and their Zinc(II) and Palladium(II) Complexes
Author(s) -
Brückner Christian,
Atoyebi Adewole O.,
Girouard Derek,
Lau Kimberly S. F.,
Akhigbe Joshua,
Samankumara Lalith,
Damunupola Dinusha,
Khalil Gamal E.,
Gouterman Martin,
Krause Jeanette A.,
Zeller Matthias
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901727
Subject(s) - chemistry , palladium , porphyrin , zinc , free base , metal , nuclear magnetic resonance spectroscopy , structural isomer , medicinal chemistry , planarity testing , photochemistry , metalation , ligand (biochemistry) , stereochemistry , crystallography , organic chemistry , catalysis , salt (chemistry) , biochemistry , receptor
While the direct, one‐step conversion of meso ‐tetrakis(pentafluorophenyl)porphyrin to its corresponding bacteriodilactone is well established, no such reaction has been achieved for meso ‐tetraphenyl or meso ‐tetrakis(4‐trifluoromethylphenyl)porphyrin. Thus, we describe two stepwise oxidation approaches of these porphyrins toward the corresponding bacteriodilactones, as mixtures of two inseparable regioisomers. As shown by 1 H NMR spectroscopy, the ratio of the two isomers is oxidant‐dependent. Their Zn II and Pd II complexes were formed by metal ion insertion into the free bases. Some of the free base dilactones and their metal complexes were also characterized crystallographically, demonstrating the planarity of the macrocycle. This report makes these intriguing porphyrinoids synthetically accessible for further study.