Self‐Assembled Multilayer‐Stabilized Nickel Nanoparticle Catalyst for Ligand‐Free Cross‐Coupling Reactions: <i>in situ</i> Metal Nanoparticle and Nanospace Simultaneous Organization

Hoshiya, Naoyuki; Fujiki, Katsumasa; Taniguchi, Takahisa; Honma, Tetsuo; Tamenori, Y.; Xiao, Mincen; Saito, Nozomi; Yokoyama, Mami; Ishii, Akira; Fujioka, Hiromichi; Shuto, Satoshi; Sato, Yoshihiro; Arisawa, Mitsuhiro

doi:10.1002/adsc.201600024

Cited by 17 publications

(19 citation statements)

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“…A comparison of the XANES spectrum of SANi(0) with those of standard materials suggests that the sulfur in SANi(0) is strongly oxidized and present as SO 4 2− . 23) The chemical shift of the sulfur in SANi(0) is similar to that previously reported for SAPd(0). These results strongly indicate that SANi(0) consists of a matrix containing SO 4 2− and is similar to SAPd(0), which consists of Pd(0) NPs implanted in a matrix formed by complexation of SO 4 2− and p-xylene.…”

Section: Sani(0) Characterizationsupporting

confidence: 85%

“…Thus the three-dimensional diversity-oriented conformational restriction strategy using our Pd NPs catalyst, SAPd(0), works effectively in the privileged structure library. 23) The structure of SAPd(0) clarified by the present analysis is indicated in Fig. 19.…”

Section: Measurement Of Pd Amount In Sadp(0) and In Reaction Mixturementioning

confidence: 69%

“…In the beginning, we developed a suitable method to prepare a SARu(0) catalyst that can be used repeatedly for ligand-free Suzuki-Miyaura coupling. The three-step method developed to prepare SARu(0), which is based on our reported method for SAPd(0) preparation, [11][12][13][14][15][16][17][18][19][20][21][22][23] is shown in Chart 17.…”

Section: Saru(0) Preparation and Catalytic Activity In Suzuki-miyauramentioning

confidence: 99%

“…[11][12][13][14][15][16][17][18][19][20][21][22] We also introduce the chemical and structural properties of SAPd(0) by spectroscopic analysis. 23) Transmission electron microscopy (TEM) analyses and extended X-ray absorption fine structure (EXAFS) experiments were performed to clarify the geometrical properties of Pd catalysis in SAPd(0). X-ray absorption near-edge structure (XANES) analysis 24) at S and C K-edge were used to determine the chemical states of sulfur and carbon in SAPd(0).…”

Section: Introductionmentioning

confidence: 99%

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Development of Metal Nanoparticle Catalysis toward Drug Discovery

Arisawa

2019

Chem. Pharm. Bull.

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Transition-metal nanoparticles (NPs) catalysts supported on solid material represent one of the most important subjects in organic synthesis due to their reliable carbon-carbon or carbon-heteroatom bondforming cross-coupling reactions. Therefore methodologically and conceptually novel immobilization methods for nonprecious transition-metal NPs are currently required for the development of organic, inorganic, green, materials, and medicinal chemistry. We discovered a self-assembled Au-supported Pd NPs catalyst (SAPd(0)) and applied it as a catalyst to Suzuki-Miyaura coupling, Buchwald-Hartwig reaction, Carbon(sp 2 and sp 3 )-Hydrogen bond functionalization, double carbonylation, removal of the allyl protecting groups of allyl esters, and redox switching. SAPd(0) comprises approximately 10 layers of self-assembled Pd(0) NPs, whose size is less than 5 nm on the surface of a sulfur-modified Au. The Pd NPs are wrapped in a sulfated p-xylene polymer matrix. We thought that the self-assembled Au-supported Pd NPs could be made by in situ metal NP and nanospace simultaneous organization (PSSO). This methodology involves 4 kinds of simultaneous procedures: i) reduction of a higher valence metal salt, ii) growth of metal NPs with appropriate size, iii) growth of a matrix with appropriate pores, and iv) wrapping of the metal NPs by matrix nanopores. This methodology is different from previously reported metal NPs-immobilizing methods, which use solid supports with preformed pores or coordination sites. We also applied the in situ PSSO method to prepare various immobilized transition-metal NPs, including base metals. For example, the in situ PSSO method can be applicable to easily prepare Ni, Ru, and Fe NPs with good recyclability and low metal leaching for use in organic synthesis. . His current research interest is in organic chemistry toward the development of medicinal chemistry. 735 Chem. Pharm. Bull. indicate that the sulfur on Au was reduced and had chemically bonded with Pd during Pd adsorption. In Pd 2p core-level photoemission spectra, the peaks from A appear close to the metallic Pd peak. These results suggest that, in the case of A, Pd(dba) 2 molecules were changed to zerovalent molecules or metallic Pd, as summarized in Fig. 4.Single crystal Au(111)/mica is not versatile. Eventually, instead of Au(111)/mica, we used Au foil and mesh to prepare B and C according to the Pd-adsorption procedure for A. When A, B, or C was subjected to the Suzuki-Miyaura coupling of 1a and 2a, the yields of the product 3a for runs 1 to 10 were excellent to quantitative in all cases, as shown in Table 1, entries 1-3. Entry 4 indicates that Material D, which was prepared from Au(mesh) with Pd(OAc) 2 as a Pd-source, was also highly active for the Suzuki-Miyaura coupling. These results show that the Pd materials A, B, C, and D are highly reactive and recyclable in this reaction.Next, we measured the amount of Pd on the Pd materials B-D using inductively coupled plasma mass spectrometry (ICP-MS) analysis. These analyses showed that in ...

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Section: Sani(0) Characterizationsupporting

confidence: 85%

Section: Measurement Of Pd Amount In Sadp(0) and In Reaction Mixturementioning

confidence: 69%

Section: Saru(0) Preparation and Catalytic Activity In Suzuki-miyauramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Development of Metal Nanoparticle Catalysis toward Drug Discovery

Arisawa

2019

Chem. Pharm. Bull.

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“…Nickel (Ni) nanoparticles (NPs) have been intensively explored due to their various potential applications, such as magnetic materials [ 1 – 3 ] and steam reforming catalyst [ 4 , 5 ]. Moreover, Ni NPs have also been investigated as a charge storage medium for nonvolatile memory devices [ 6 – 12 ], which could be attributed to some potential advantages of Ni NPs, including high density of states around the Fermi level, strong charge confinement, a high work function of 5.2 eV, and low diffusivity.…”

Section: Introductionmentioning

confidence: 99%

Plasma-Assisted Atomic Layer Deposition of High-Density Ni Nanoparticles for Amorphous In-Ga-Zn-O Thin Film Transistor Memory

et al. 2017

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For the first time, the growth of Ni nanoparticles (NPs) was explored by plasma-assisted atomic layer deposition (ALD) technique using NiCp2 and NH3 precursors. Influences of substrate temperature and deposition cycles on ALD Ni NPs were studied by field emission scanning electron microscope and X-ray photoelectron spectroscopy. By optimizing the process parameters, high-density and uniform Ni NPs were achieved in the case of 280 °C substrate temperature and 50 deposition cycles, exhibiting a density of ~1.5 × 1012 cm−2 and a small size of 3~4 nm. Further, the above Ni NPs were used as charge storage medium of amorphous indium-gallium-zinc oxide (a-IGZO) thin film transistor (TFT) memory, demonstrating a high storage capacity for electrons. In particular, the nonvolatile memory exhibited an excellent programming characteristic, e.g., a large threshold voltage shift of 8.03 V was obtained after being programmed at 17 V for 5 ms.

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Carbon(sp²)‐carbon(sp³) Bond‐forming Cross‐coupling Reactions Using Sulfur‐Modified Au‐Supported Nickel Nanoparticle Catalyst

et al. 2022

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We report a carbon(sp2)‐carbon(sp3) bond‐forming cross‐coupling reactions by employing a nano‐size nickel catalyst supported on sulfur‐modified gold (SANi). This transformation demonstrates an efficient synthesis of functionalized aryl compounds, including heterocycles. Notably, the reactions proceeded in good yields with significantly low leaching of nickel from SANi. Moreover, SANi could be recycled several times without significant loss of catalytic activity.

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Self‐Assembled Multilayer‐Stabilized Nickel Nanoparticle Catalyst for Ligand‐Free Cross‐Coupling Reactions: in situ Metal Nanoparticle and Nanospace Simultaneous Organization

Cited by 17 publications

References 50 publications

Development of Metal Nanoparticle Catalysis toward Drug Discovery

Development of Metal Nanoparticle Catalysis toward Drug Discovery

Plasma-Assisted Atomic Layer Deposition of High-Density Ni Nanoparticles for Amorphous In-Ga-Zn-O Thin Film Transistor Memory

Carbon(sp²)‐carbon(sp³) Bond‐forming Cross‐coupling Reactions Using Sulfur‐Modified Au‐Supported Nickel Nanoparticle Catalyst

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Self‐Assembled Multilayer‐Stabilized Nickel Nanoparticle Catalyst for Ligand‐Free Cross‐Coupling Reactions: in situ Metal Nanoparticle and Nanospace Simultaneous Organization

Cited by 17 publications

References 50 publications

Development of Metal Nanoparticle Catalysis toward Drug Discovery

Development of Metal Nanoparticle Catalysis toward Drug Discovery

Plasma-Assisted Atomic Layer Deposition of High-Density Ni Nanoparticles for Amorphous In-Ga-Zn-O Thin Film Transistor Memory

Carbon(sp2)‐carbon(sp3) Bond‐forming Cross‐coupling Reactions Using Sulfur‐Modified Au‐Supported Nickel Nanoparticle Catalyst

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Carbon(sp²)‐carbon(sp³) Bond‐forming Cross‐coupling Reactions Using Sulfur‐Modified Au‐Supported Nickel Nanoparticle Catalyst