Nickel: The “Spirited Horse” of Transition Metal Catalysis

Ananikov, Valentine P.

doi:10.1021/acscatal.5b00072

Cited by 698 publications

(401 citation statements)

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“…Over recent decades, the use of asymmetric nickel catalysts has substantially evolved both in acid–base and redox catalysis456. Several examples of chiral nickel complexes that act as asymmetric catalysts have been sporadically characterized by X-ray structure analysis, opening up a window of opportunity to discuss the stereo-discrimination process in asymmetric nickel catalysis7891011121314151617.…”

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confidence: 99%

Naked d-orbital in a centrochiral Ni(II) complex as a catalyst for asymmetric [3+2] cycloaddition

et al. 2017

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Chiral metal catalysts have been widely applied to asymmetric transformations. However, the electronic structure of the catalyst and how it contributes to the activation of the substrate is seldom investigated. Here, we report an empirical approach for providing insights into the catalytic activation process in the distorted Ni(II)-catalysed asymmetric [3+2] cycloaddition of α-ketoesters. We quantitatively characterize the bonding nature of the catalyst by means of electron density distribution analysis, showing that the distortion around the Ni(II) centre makes the dz2 orbital partially ‘naked', wherein the labile acetate ligand is coordinated with electrostatic interaction. The electron-deficient dz2 orbital and the acetate act together to deprotonate the α-ketoester, generating the (Λ)-Ni(II)–enolate. The solid and solution state analyses, together with theoretical calculations, strongly link the electronic structure of the centrochiral octahedral Ni(II) complex and its catalytic activity, depicting a cooperative mechanism of enolate binding and outer sphere hydrogen-bonding activation.

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Naked d-orbital in a centrochiral Ni(II) complex as a catalyst for asymmetric [3+2] cycloaddition

et al. 2017

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“…[1] Recently, nickel catalysis has emerged in the synthetic community as an exceptionally useful strategy for cross-coupling. [2] Although tremendous advances in nickel-catalyzed carbon–carbon bond formation have been achieved (e.g., Negishi, Suzuki, Stille, Kumada, Hiyama couplings), [3] nickel-catalyzed carbon–oxygen bond forming processes have proven significantly more challenging. The rationale behind this is that reductive elimination of Ni(II) alkoxide complexes is often cited as being significantly challenging even at elevated temperatures.…”

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Nickel‐Catalyzed Intramolecular C−O Bond Formation: Synthesis of Cyclic Enol Ethers

2016

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An efficient and exceptionally mild intramolecular nickel-catalyzed carbon–oxygen bond-forming reaction between vinyl halides and primary, secondary, and tertiary alcohols has been achieved. Zinc powder was found to be an essential additive for obtaining high catalyst turnover and yields. This operationally simple method allows direct access to cyclic vinyl ethers in high yields in a single step.

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“…In Figure 7 ( It must be emphasized that even though we demonstrate the effectiveness of this egg-shell catalyst for ammonia decomposition reaction, the application of this synthesis route could be far more general. For example, this could be a way to maximum utilization of noble metals, such as Pt and reduce the catalyst cost in the process [67].…”

Section: Egg-shell Uniformmentioning

confidence: 99%

Synthesis and characterization of Fe–Ni/ɣ-Al2O3 egg-shell catalyst for H2 generation by ammonia decomposition

Silva¹,

Nielsen²,

Fiordaliso³

et al. 2015

Applied Catalysis A: General

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Nickel: The “Spirited Horse” of Transition Metal Catalysis

Cited by 698 publications

References 109 publications

Naked d-orbital in a centrochiral Ni(II) complex as a catalyst for asymmetric [3+2] cycloaddition

Naked d-orbital in a centrochiral Ni(II) complex as a catalyst for asymmetric [3+2] cycloaddition

Nickel‐Catalyzed Intramolecular C−O Bond Formation: Synthesis of Cyclic Enol Ethers

Synthesis and characterization of Fe–Ni/ɣ-Al2O3 egg-shell catalyst for H2 generation by ammonia decomposition

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