镍催化芳烃卤化物还原性交叉偶联的反应机理

doi:10.3866/PKU.WHXB201403241

Abstract

Abstract:

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.

Key words: Density functional theory, Nickel catalysis, Reductive cross-coupling, Reaction mechanism, Unsymmetrical biaryl

MSC2000:

O641

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JIANG Feng, REN Qing-Hua. Reaction Mechanism for the Ni-Catalyzed Reductive Cross-Coupling of Aryl Halides[J].Acta Phys. -Chim. Sin., 2014, 30(5): 821-828.

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

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