EFFICIENT PERIPHERAL FUNCTIONALIZATION OF PORPHYRINS

Article abstract of DOI:10.1016/0040-4020(82)80211-1

Details are given for the mild and efficient synthesis of β-substituted "capped"-porphyrins and meso-tetraphenylporphyrins from the corresponding porphyrins.The nitro derivatives are cleanly reduced to β-aminoporphyrins, which are susceptible to hydrolysis but otherwise may be further derivatized on nitrogen by standard procedures.Treatment of β-nitroporphyrins with thiolate ions in DMF gave β-alkylthioporphyrins, β-arylthioporphyrins or the corresponding denitrated porphyrin, depending on the tiol.