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Updated: Jul 10, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Cu-catalyzed Goldberg and Ullmann reactions of aryl halides using chelating N- and O-based ligands
Ryan A Altman1, Stephen L Buchwald
1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-490, Cambridge, Massachusetts 02139, USA.
Abstract:
The following protocol can be applied in the selective cross-coupling reaction of an amine with an aryl iodide or bromide using a copper (Cu)-based catalyst to provide the corresponding N-aryl amine. The general procedure described in this text includes a detailed description of an appropriate reaction setup, two methods for assaying the crude reaction mixture (gas chromatography and thin layer chromatography) and a procedure for the isolation, purification and characterization of the anticipated product. Manipulation of the reagents can be done in the air, without the use of a glovebox; however, the cross-coupling reactions must be performed in a sealed reactor under an inert atmosphere. Three C-N bond-forming reactions are included in the protocol as representative examples of this procedure. Although the reactions can proceed in <1 h, the protocols, including workup, generally take 6-30 h to complete.
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