Highly selective bromination of tetramesitylporphyrin: An easy access to robust metalloporphyrins, M-Br8TMP and M-Br8TMPS

Article abstract of DOI:10.1016/S0040-4039(00)88897-8

The N-bromosuccinimide bromination of the zinc derivative of meso-tetramesitylporphyrin, Zn(TMP), in methanol at reflux in air, gives the corresponding (β-pyrrole)octabromo derivative, meso-tetramesityl-β-octabromoporphyrinatozinc, Zn(Br₈TMP), in high yield (60-75%). Furthermore, the sulfonation by oleum of the metal-free ligand gives the persulfonated porphyrin, meso-tetrakis(3,5-disulfonatomesityl)-β-octabromoporphyrin, Br₈ TMPSH₂ (70-75%). These robust manganese and iron derivatives are efficient catalysts in oxygen atom or electron transfer reactions.