| Summary: | <i>meso</i>-Phenyl- and <i>meso</i>-pentafluorophenyl-porpholactones, their metal complexes, as well as porphyrinoids directly derived from them are useful in a number of technical and biomedical applications, and more uses are expected to be discovered. About a dozen competing and complementary pathways toward their synthesis were reported. The suitability of the methods changes with the <i>meso</i>-aryl group and whether the free base or metal derivatives are sought. These circumstances make it hard for anyone outside of the field of synthetic porphyrin chemistry to ascertain which pathway is the best to produce which specific derivative. We report here on what we experimentally evaluated to be the most efficient pathways to generate the six key compounds from the commercially available porphyrins, <i>meso</i>-tetraphenylporphyrin (TPP) and <i>meso</i>-tetrakis(pentafluorophenyl)porphyrin (T<sup>F</sup>PP): free base <i>meso</i>-tetraphenylporpholactone (TPL) and <i>meso</i>-tetrakis(pentafluorophenyl)porpholactone (T<sup>F</sup>PL), and their platinum(II) and zinc(II) complexes TPLPt, T<sup>F</sup>PLPt, TPLZn, and T<sup>F</sup>PLZn, respectively. Detailed procedures are provided to make these intriguing molecules more readily available for their further study.
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