The recent development of palladium-catalyzed cross-coupling reactions between mono-, di-, and tetrasubstituted bromo-porphyrins and amides, amines, alcohols, and thiols has allowed for the preparation of a number of chiral porphyrin analogs. Metalated derivatives of these chiral porphyrins have been used to catalyze a number of key functional group transformations with good diastereo- and enantioselectivity. Despite the progress that has been made in the development of these catalysts, two key problems still exist. First, the hydrophobic nature of the porphyrin ring makes these systems insoluble in most polar solvents, limiting substrate scope. In addition, the aromatic nature of the porphyrin ring facilitates pi stacking with some existing porphyrin catalysts, resulting in aggregation and decreased turnover. In an effort to address these problems, we have started synthesizing novel porphyrins bearing carbohydrate residues using a palladium-catalyzed cross-coupling approach. Here we present the preliminary results of our research.

Synthesis of carbohydrate-porphyrins conjugates via palladium-catalyzed cross-coupling approach

239th National Meeting (2010)

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