Nitroethylation of Vinyl Triflates and Bromides.

TLDR: In this article, a two-carbon homologation of vinyl triflates and bromides for the synthesis of homoally-lic nitro products is described, which exploits the anion stabilizing and leaving group properties of nitromethane.

Abstract: A two-carbon homologation of vinyl triflates and bromides for the synthesis of homoallylic nitro products is described. This palladium-catalyzed double coupling of nitromethane exploits the anion stabilizing and leaving group properties of nitromethane, generating the homo allyl nitro products via a tandem cross-coupling/π-allylation sequence. The resultant process provides a mild and convenient entry to nitroethylated products, which are versatile precursors to β,γ-unsaturated carbonyls, homoallylic amines, and nitrile oxides.