Citation: JIANG Feng, REN Qing-Hua. Reaction Mechanism for the Ni-Catalyzed Reductive Cross-Coupling of Aryl Halides[J]. Acta Physico-Chimica Sinica, ;2014, 30(5): 821-828. doi: 10.3866/PKU.WHXB201403241 shu

Reaction Mechanism for the Ni-Catalyzed Reductive Cross-Coupling of Aryl Halides

JIANG Feng ,
REN Qing-Hua

1.
Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, P. R. China

Received Date: 10 December 2013
Available Online: 24 March 2014
Fund Project:

The mechanism of the Ni-catalyzed reductive cross-coupling reaction of bromobenzene (R₁) and methyl 4-bromobenzoate (R₂) to form an unsymmetrical biaryl system has been theoretically investigated using density functional theory calculations. Our results showed that the Ni⁰-catalyzed process was favored over the NiI-catalyzed mechanism. The mechanism for the reaction of the Ni⁰ catalyst initially attacking either R₁ or R₂ was quite similar, where the energy barrier in the gas phase for the rate-limiting step was 70.50 or 49.66 kJ·mol^-1, respectively. The mechanism in the favored Ni⁰-catalyzed reaction involved the following steps: first oxidative addition, reduction, second oxidative addition, reductive elimination, and catalyst regeneration. Our calculated results also indicated that no organometallic reagents were produced in the reaction cycle.
- Density functional theory,
- Nickel catalysis,
- Reductive cross-coupling,
- Reaction mechanism,
- Unsymmetrical biaryl
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