ORGN 155 |
| X. Peter Zhang, Guangyao Gao, and Ying Chen. Department of Chemistry, University of Tennessee, 614 Buehler Hall, Knoxville, TN 37996 |
| The biologically important porphyrins are generally synthesized via acid-catalyzed multiple condensations of monopyrroles or dipyrrolic intermediates with aldehydes, followed by oxidation. Owing to the inherent unfavorable entropy associated with multiple condensation reactions along with the acidic and oxidative conditions, the classic synthesis of porphyrins typically gives low yields, requires tedious purification and restrains efficient preparation of porphyrins derivatives with functional and sensitive groups. Recently, a synthetic strategy involving the applications of transition metal-mediated cross-coupling reactions of preformed halogenated porphyrins has proved advantageous, allowing efficient synthesis of a large number of derivatives from a single halogenated porphyrin precursor. Based on this powerful new strategy, we have recently developed several general methodologies for efficient synthesis of porphyrins with nitrogen, oxygen and other heteroatom-based substitutents via metal-catalyzed carbon-heteroatom cross-coupling reactions. The detailed synthesis and structural features of this new family of porphyrins will be presented. |
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |