Dendritic metalloporphyrins as catalysts for organic transformations

Abstract

Dendritic manganese, iron, and ruthenium porphyrins with dendritic wedges attached to the periphery of meso-tetraphenylporphyrin (TPP) or meso-triarylporphyrin macrocycle were reported to be active catalysts for epoxidation or cyclopropanation of alkenes or oxidation of sulfides. The dendritic manganese and iron porphyrin catalysts exhibit considerably higher regioselectivity and shape selectivity than the respective parent catalyst [M(TPP)Cl] (M = Mn, Fe). Systematic increase in shape selectivity, diastereoselectivity, epoxide/sulfoxide selectivity, or catalyst stability with increasing generation number of the dendritic wedges is observed for the alkene epoxidation or sulfide oxidation reactions catalyzed by these dendritic manganese, iron, and ruthenium porphyrins. © 2003 Académie des sciences. Published by Éditions scientifiques et médicales Elsevier SAS. All rights reserved.