Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2007, Issue 9, Pages 1423-1428Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200700005
Keywords
homogeneous catalysis; amination; phosphanes; conducting materials
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The Pd-mediated Buchwald-Hartwig amination reaction of aryl halides in a phosphonium salt ionic liquid consisting of a trihexyl(tetradecyl)phosphonium cation with a range of anions has been investigated. A pronounced anionic effect was uncovered with the reaction proceeding readily with weakly nucleophilic diarylamines only in the presence of noncoordinating anions. A mechanism is postulated to explain these results and it involves a rate-limiting ligand exchange step that proceeds through a dissociative pathway.
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