ORGN 146 |
| We are interested in developing catalytic palladium-coupling methods to generate well-defined dihydroxyindole oligomers inspired by the human pigment, eumelanin. Indoles are widely used as one component in Suzuki reactions, but indole-indole couplings by this method are relatively undeveloped. In the course of our work on the Suzuki reaction, the Pd-catalyzed homo-coupling of indole boronic acids emerged as a potent alternative. We are optimizing the reaction for indoles and other aryl boronic acids. Our preliminary results indicate it is possible to obtain yields as high as ninety-four percent while running the reaction at room temperature in as short as 1.5 hours. Variation in the percentage of catalyst and temperature were explored to determine the optimum conditions under which homo-coupling occurs. Appling our new aryl coupling methodology to indole derivatives provided a novel approach for the iterative synthesis of oligomers related to eumelanin. |
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Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |