Chiral metal nanoparticle-catalyzed asymmetric C–C bond formation reactions

Yasukawa, Tomohiro; Miyamura, Hiroyuki; Kobayashi, Shū

doi:10.1039/c3cs60298b

Cited by 161 publications

(88 citation statements)

References 156 publications

(161 reference statements)

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“…Heterogeneous asymmetric catalysts with bimetallic NPs have also been successfully developed in recent years. 91 Kobayashi and coworkers demonstrated that polymer-incarcerated chiral Rh/Ag NPs are effective for the asymmetric 1,4-addition reactions of arylboronic acids to α,β-unsaturated carbonyl compounds. [103][104] The composition of the bimetallic Rh/Ag NP and the type of chiral ligand affected catalytic activity and the amount of metal leaching.…”

Section: Chiral Ligands and Modifiers For Asymmetric Catalysismentioning

confidence: 99%

“…[87][88][89][90][91][92] Such catalysts can be more useful than the traditional homogeneous asymmetric catalysts due to the advantages of easy separation, efficient recycling, and overall lower costs. For example, palladium NPs modified by chiral ligands has drawn much attention in the field of asymmetric catalysis [93][94][95][96] (the in-depth discussion of these systems is outside the scope of this Perspective, as the discrimination between homogeneous and heterogeneous catalysis is often challenging for Pd catalysts).…”

Section: Chiral Ligands and Modifiers For Asymmetric Catalysismentioning

confidence: 99%

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Controllable Catalysis with Nanoparticles: Bimetallic Alloy Systems and Surface Adsorbates

2016

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Transition metal nanoparticles are privileged materials in catalysis due to their high specific surface areas and abundance of active catalytic sites. While many of these catalysts are quite useful, we are only beginning to understand the underlying catalytic mechanisms. Opening the "black box" of nanoparticle catalysis is essential to achieve the ultimate goal of catalysis by design. In this Perspective we highlight recent work addressing the topic of controlled catalysis with bimetallic alloy and "designer" adsorbate-stabilized metal nanoparticles.

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Section: Chiral Ligands and Modifiers For Asymmetric Catalysismentioning

confidence: 99%

Section: Chiral Ligands and Modifiers For Asymmetric Catalysismentioning

confidence: 99%

Controllable Catalysis with Nanoparticles: Bimetallic Alloy Systems and Surface Adsorbates

2016

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“…Functionalization of metal NPs using chiral ligands have been used for enantioselective catalysis. [31] These developments are opening new aspects in tailoring colloidal NPs for catalytic processes whereby ligands are not merely spectator species but play a role in mediating the reaction through specific interactions with reacting species, similar to ligand acceleration effects in homogeneous systems. From a NP design perspective, manipulating surface chemistry through functionalization can be achieved by ligand exchange in many colloidal systems.…”

Section: Molecular Engineering Of the Nanoparticle Surfacesmentioning

confidence: 99%

Engineering Metallic Nanoparticles for Enhancing and Probing Catalytic Reactions

Collins

Holmes

2016

Advanced Materials

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Type of publicationArticle (peer-reviewed) AbstractRecent developments in tailoring the structural and chemical properties of colloidal nanoparticles (NPs) have led to significant enhancements in catalyst performance. Controllable colloidal NP synthesis has also allowed tailor-made NPs to also serve as mechanistic probes for catalytic processes. The innovative use of colloidal NPs to gain fundamental insights into catalytic function will be highlighted across a variety of catalytic applications. The future engineering of catalyst NPs is also moving beyond size, shape and composition considerations.Advancements in understanding structure-property relationships have enabled incorporation of complex features such as tuning surface strain to influence the behaviour of catalytic NPs.Exploiting plasmonic properties of NPs and altering colloidal surface chemistry through functionalization are also emerging as important areas for rational design of catalytic NPs. This news article will highlight the key developments and challenges to future design of catalytic NPs.

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“…Even if more and more organic transformations are using metal nanoparticles (MNPs) as catalysts [1][2][3][4][5][6], few of them concern enantioselective processes (for selected reviews, see [7][8][9][10]). The enantioselective catalysis on surfaces is commonly explained by three main mechanisms: the presence of chiral crystalline atomic structures at the surface, chiral adsorbates which modify the surface and chiral modifiers which control the approach of the substrate on the surface [11,12].…”

Section: Introductionmentioning

confidence: 99%

P-Stereogenic Phosphines for the Stabilisation of Metal Nanoparticles. A Surface State Study

et al. 2016

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Palladium and ruthenium nanoparticles have been prepared following the organometallic precursor decomposition methodology, under dihydrogen pressure and in the presence of borane protected P-stereogenic phosphines. NMR (Nuclear Magnetic Resonance) monitoring of the corresponding syntheses has permitted to determine the optimal metal/ligand ratio for leading to small and well-dispersed nanoparticles. Exchange ligand reactions of the as-prepared materials have proven the strong interaction of the phosphines with the metal surface; only oxidative treatment using hydrogen peroxide could release the phosphine-based stabiliser from the metal surface. Pd and Ru nanoparticles have been evaluated in hydrogenation reactions, confirming the robustness of the stabilisers, which selectively permitted the hydrogenation of exocyclic C=C bonds, preventing the coordination of the aromatic rings and as a result, their hydrogenation.

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Chiral metal nanoparticle-catalyzed asymmetric C–C bond formation reactions

Abstract: Chiral ligand-modified metal nanoparticles possess an attractive potential for application in asymmetric synthesis. This article focuses on chiral-nanoparticle-catalyzed asymmetric C-C bond formation reactions and discusses the nature of the active species.

Cited by 161 publications

References 156 publications

Controllable Catalysis with Nanoparticles: Bimetallic Alloy Systems and Surface Adsorbates

Controllable Catalysis with Nanoparticles: Bimetallic Alloy Systems and Surface Adsorbates

Engineering Metallic Nanoparticles for Enhancing and Probing Catalytic Reactions

P-Stereogenic Phosphines for the Stabilisation of Metal Nanoparticles. A Surface State Study

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