Buchwald-Hartwig aminations of aryl chlorides: A practical protocol based on commercially available Pd(0)-NHC catalysts

Commercially available, air- and water-stable naphthoquinone imidazolin-2-ylidene-palladium(0) complexes were found to be highly active one-component catalysts for the amination of aryl halides. With these very robust catalysts, the expensive bases CS2CO3 or NaOt-Bu traditionally used can be replace...

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Bibliographic Details
Published inSynlett no. 2; pp. 275 - 278
Main Authors Goossen, LJ, Paetzold, J, Briel, O, Rivas-Nass, A, Karch, R, Kayser, B
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.02.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
aryl chlorides
CROSS-COUPLING REACTIONS
HIGHLY-ACTIVE CATALYST
LIGANDS
carbene ligands
ROOM-TEMPERATURE AMINATION
palladium
PALLADIUM CARBENE
amination
HETEROCYCLIC CARBENE COMPLEX
OXIDATIVE ADDITION
BROMIDES
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Summary:Commercially available, air- and water-stable naphthoquinone imidazolin-2-ylidene-palladium(0) complexes were found to be highly active one-component catalysts for the amination of aryl halides. With these very robust catalysts, the expensive bases CS2CO3 or NaOt-Bu traditionally used can be replaced by KOH. A convenient reaction protocol has been developed for the coupling of a wide range of aryl chlorides with primary or secondary amines.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-837205