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Updated: Jul 13, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
The first N-heterocyclic carbene-based nickel catalyst for C-S coupling
Yugen Zhang1, Kao Chin Ngeow, Jackie Y Ying
1Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos, Singapore 138669, Singapore. ygzhang@ibn.a-star.edu.sg
New nickel-N-heterocyclic carbene (NHC) catalysts efficiently catalyze carbon-sulfur (C-S) coupling reactions. These inexpensive and eco-friendly catalysts show promise for replacing palladium-based systems in C-S bond formation.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Organic Synthesis
Background:
- Carbon-sulfur (C-S) coupling reactions are crucial for synthesizing organosulfur compounds.
- Palladium-organophosphane catalysts are widely used but can be expensive and toxic.
- Development of alternative, cost-effective, and sustainable catalysts is needed.
Purpose of the Study:
- To develop novel N-heterocyclic carbene (NHC)-based transition metal catalysts for C-S coupling.
- To investigate the efficacy of nickel-NHC catalysts in C-S coupling reactions.
- To evaluate the influence of NHC ligand properties on catalytic activity.
Main Methods:
- Synthesis of novel nickel-N-heterocyclic carbene (Ni-NHC) complexes.
- Application of Ni-NHC catalysts in C-S coupling reactions with various aryl halides.
- Systematic variation of NHC ligand electronic and steric properties.
Main Results:
- The developed Ni-NHC catalysts demonstrated good to excellent activity in C-S coupling reactions.
- Catalytic performance was significantly influenced by the electronic and steric characteristics of the NHC ligands.
- The Ni-NHC catalysts proved to be inexpensive, easily synthesized, and environmentally benign.
Conclusions:
- Nickel-N-heterocyclic carbene complexes are effective catalysts for C-S coupling reactions.
- Ligand design plays a critical role in optimizing the performance of Ni-NHC catalysts.
- These novel catalysts offer a sustainable and economical alternative to traditional palladium-based systems for C-S coupling.
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