Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids.
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.
Law
Man Chun
MC
Department of Chemistry, McGill University, Montreal, Quebec, Canada H3A 2K6.
Cheung
Tin Wai
TW
Wong
Kwok-Yin
KY
Chan
Tak Hang
TH
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
D000498:Allyl Compounds; D000588:Amines; D006842:Hydrocarbons, Brominated; D007097:Imines; D052578:Ionic Liquids; D009942:Organometallic Compounds; D007204:Indium