title: Nitroethylation of vinyl triflates and bromides.
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.
authors.affiliation: Penn Merck High Throughput Experimentation Laboratory, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Rosaura
authors.initials: R
authors.lastname: Padilla-Salinas
authors.forename: Ryan R
authors.initials: RR
authors.lastname: Walvoord
authors.forename: Sergei
authors.initials: S
authors.lastname: Tcyrulnikov
authors.forename: Marisa C
authors.initials: MC
authors.lastname: Kozlowski
mesh_terms: D000478:Alkylation; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D008698:Mesylates / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D001965:Bromides; D008698:Mesylates; D009574:Nitro Compounds; D014753:Vinyl Compounds; C437735:vinyl triflate; D010165:Palladium