ORGN 136 |
Our research group has recently reported a new efficient copper and rhodium catalyzed methylenation of carbonyl derivatives using TMSCHN2, i-PrOH, Ph3P. We have also devised multicatalytic strategies to in-situ derivatized the terminal alkenes. Along these lines, this paper will feature a new methylenation-Heck coupling multicatalytic tandem reactions which lead to the formation of substituted alkenes directly from carbonyl compounds. Copper catalyzed-methylenation reaction with benzaldehyde derivatives led to the formation of the corresponding styrenes, which are then in-situ submitted to the palladium-catalyzed Heck coupling reaction. This one-pot sequence avoided the isolation of volatile styrene intermediates, and decreased also the amount of by-products. We have used this one-pot process to synthesize biologicaly active stilbene derivatives such as the resveratrol analogues. Furthermore, the extension of this method to an intramolecular process will be also presented.
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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 |