Nitroethylation of Vinyl Triflates and Bromides
Rosaura Padilla-Salinas, Ryan R. Walvoord, Sergei Tcyrulnikov and Marisa C. Kozlowski*
*Penn Merck High Throughput Experimentation Laboratory, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States, Email: marisasas.upenn.edu
R. Padilla-Salinas. R. R. Walvoord, S. Tcyrulnikov, M. C. Kozlowski, Org. Lett., 2013, 15, 3966-3969.
A palladium-catalyzed double coupling of nitromethane with vinyl triflates and bromide generates homo allyl nitro products via a tandem cross-coupling/π-allylation sequence. The resultant process exploits the anion stabilizing and leaving group properties of nitromethane and provides a mild and convenient entry to nitroethylated products, which are versatile precursors to β,γ-unsaturated carbonyls, homoallylic amines, and nitrile oxides.
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