ORGN 162 |
| Virgil Percec, Geoffrey M. Golding, Jan Smidrkal, and Oliver Weichold. Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, PA 19104-6323 |
| The use of nickel in the Suzuki cross-coupling of aryl sulfonates and aryl halides was investigated in detail. The reaction was optimized to give good yields for both electron-rich and electron-poor substrates. It was found that NiCl2(dppe) with an additional two equilvalents of PPh3 gave the most active catalytic species. This catalyst system was able to cross-couple the traditionally less reactive, electron-rich aryl chlorides and sulfonates. Also investigated is the cross-coupling of pinacol borane with aryl halides in a one pot, nickel-catalyzed reaction. This reaction can be utilized to make boronic acids in substrates where lithiation or Grignard species are not possible. The utility of these reactions in the synthesis of para and meta phenylene oligimers will also be discussed |
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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 |