Highly Selective Bromination of Tetramesitylporphyrin: An Easy Access to Robust Metalloporphyrins, M-Br8TMP and M-Br8TMPS. Examples of Application in Catalytic Oxygenation and Oxidation Reactions.

Abstract 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-βoctabromoporphyrinatozinc, Zn(Br 8 TMP), 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, Br 8 TMPSH 2 (70-75%). These robust manganese and iron derivatives are efficient catalysts in oxygen atom or electron transfer reactions.