title: Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids.
abstract: Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.
authors.affiliation: Department of Chemistry, McGill University, Montreal, Quebec, Canada H3A 2K6.
authors.forename: Man Chun
authors.initials: MC
authors.lastname: Law
authors.forename: Tin Wai
authors.initials: TW
authors.lastname: Cheung
authors.forename: Kwok-Yin
authors.initials: KY
authors.lastname: Wong
authors.forename: Tak Hang
authors.initials: TH
authors.lastname: Chan
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis*; D007204:Indium / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry
chemical_list: D000498:Allyl Compounds; D000588:Amines; D006842:Hydrocarbons, Brominated; D007097:Imines; D052578:Ionic Liquids; D009942:Organometallic Compounds; D007204:Indium