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Updated: Sep 30, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
A Well-Defined, Air-Stable NHC-Ni Precatalyst for C-N Bond Formation
Kianoosh Masoomi1, Jürgen Schulmeister1, Michael G Organ1
1Centre for Catalysis Research and Innovation (CCRI), Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Ontario, Canada.
Abstract:
A new, well-defined, air-stable N-heterocyclic carbene nickel(II) precatalyst [(IPr)Ni(N-methylphenethylamine)Cl] (IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) was designed, synthesized, and evaluated for C-N cross-coupling reactions. This precatalyst is readily activated in the presence of base and efficiently promotes the amination of a variety of aryl chlorides with amines. Optimization studies established robust reaction conditions and revealed the influence of electronic and steric properties of the coupling partners on catalytic performance. The combination of operational simplicity, long-term bench stability, and facile activation makes this NHC-Ni precatalyst a good choice for nickel-catalyzed C-N bond formation.
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