Organic Chemistry Portal



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:

R. Padilla-Salinas. R. R. Walvoord, S. Tcyrulnikov, M. C. Kozlowski, Org. Lett., 2013, 15, 3966-3969.

DOI: 10.1021/ol401747u


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.

see article for more examples

Key Words

nitro compounds, vinylation

ID: J54-Y2013