title: Additive-Free Pd-Catalyzed α-Allylation of Imine-Containing Heterocycles.
abstract: An additive-free Pd-catalyzed α-allylation of different imino-group-ontaining heterocycles is reported. The activation of α-CH pronucleophiles (pKa(DMSO) > 25) occurs without the addition of strong bases or Lewis acids using only the Pd/Xantphos catalyst system. The reaction scope has been studied for various 5- and 6-membered nitrogen-containing heterocycles (yields up to 96%). Mechanistic investigations suggest an initial allylation of the imine-N followed by a Pd-catalyzed formal aza-Claisen rearrangement.
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Marko
authors.initials: M
authors.lastname: Kljajic
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Johannes G
authors.initials: JG
authors.lastname: Puschnig
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Hansjörg
authors.initials: H
authors.lastname: Weber
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Rolf
authors.identifier: 0000-0001-6009-7359
authors.initials: R
authors.lastname: Breinbauer