Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids

Chun Law Man, Wai Cheung Tin, Kwok Yin Wong, Hang Chan Tak

Research output: Journal article publicationJournal articleAcademic researchpeer-review

47 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.
Original languageEnglish
Pages (from-to)923-929
Number of pages7
JournalJournal of Organic Chemistry
Volume72
Issue number3
DOIs
Publication statusPublished - 2 Feb 2007

ASJC Scopus subject areas

  • Organic Chemistry

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