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Easily Accessible and Solution-Stable Ni(0) Precatalysts for High-Throughput Experimentation.
Gilian T Thomas1, Odhran D Cruise1, Daelin Peel-Smith1
1Department of Chemistry, University of Victoria, 3800 Finnerty Rd., Victoria, BC V8P 5 C2, Canada.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 17, 2025
Summary
New N,N'-diaryl diazabutadiene (DAB) Ni(0) complexes offer stable, soluble catalysts for Suzuki and C-N coupling reactions. These complexes show high-throughput experimentation (HTE) performance comparable or superior to Ni(COD)2.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Synthetic Chemistry
Background:
- Nickel complexes are crucial catalysts in cross-coupling reactions.
- Developing stable and soluble precatalysts is essential for efficient catalytic processes.
- High-throughput experimentation (HTE) accelerates catalyst screening and optimization.
Purpose of the Study:
- To synthesize and characterize novel N,N'-diaryl diazabutadiene (DAB) Ni(0) complexes.
- To evaluate the catalytic performance of these Ni(0) complexes in Suzuki and C-N coupling reactions using HTE.
- To compare the efficacy of the new Ni(0) precatalysts against the established Ni(COD)2 standard.
Main Methods:
- Synthesis of N,N'-diaryl diazabutadiene (DAB) Ni(0) complexes stabilized by alkene ligands.
- Characterization of the synthesized Ni(0) complexes.
- Application of high-throughput experimentation (HTE) for catalyst screening.
- Evaluation of catalytic activity in Suzuki and C-N coupling reactions.
Main Results:
- The synthesized Ni(0) complexes exhibit good solubility and stability in various organic solvents.
- These DAB Ni(0) complexes demonstrated excellent performance in Suzuki and C-N coupling reactions.
- Catalytic activity was found to be equal to or better than the benchmark Ni(COD)2 catalyst.
- The complexes are suitable for in situ catalyst formation in HTE.
Conclusions:
- N,N'-diaryl diazabutadiene (DAB) Ni(0) complexes represent a promising class of precatalysts.
- These complexes offer advantages in terms of stability, solubility, and catalytic efficiency.
- Their suitability for HTE facilitates rapid catalyst discovery and optimization for cross-coupling reactions.
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