ORGN 147 |
Suzuki-Miyaura cross-coupling of potassium organotrifluoroborates
| Gary A. Molander, Luciana A. Felix, and Daniel E. Petrillo. Department of Chemistry, University of Pennsylvania, Roy and Diana Vagelos Laboratories, 231 South 34th Street, Philadelphia, PA 19104-6323 |
| Recently, potassium organotrifluoroborates (RBF3K) have been demonstrated to be highly effective coupling partners in the Suzuki-Miyaura reaction. We have shown that the palladium-catalyzed cross-coupling reaction of air-stable potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields giving the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)- conjugated dienes stereo- and regiospecifically. A variety of functional groups are tolerated in both partners. In addition, it has been shown that organotrifluoroborates are capable of withstanding oxidative conditions. This permits the use of oxidized organoboron reagents in the Suzuki-Miyaura reaction. Several epoxidized organotrifluoroborates have been prepared, and their reactivity explored. 
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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
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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