Reusable Immobilized Iron(II) Nanoparticle Precatalysts for Ligand-Free Kumada Coupling

Akiyama, Toshiki; Wada, Yasuhiko; Jenkinson, Kellie; Honma, Tetsuo; Tsuruta, Kazuki; Tamenori, Y.; Haneoka, Hitoshi; Takehara, Tsunayoshi; Suzuki, Takayoshi; Murai, Kenichi; Fujioka, Hiromichi; Sato, Yoshihiro; Wheatley, Andrew E. H.; Arisawa, Mitsuhiro

doi:10.1021/acsanm.8b01742

Cited by 10 publications

(7 citation statements)

References 75 publications

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“…Arisawa et al developed a well-established metal-nanoparticle catalyst preparative protocol by simultaneous in situ metal NPs and nanospace organization (PSSO). Several sulfur-modified Au-supported metal (Pd, Ni, Ru, and Fe) catalysts were constructed by self-assembled metal NPs, which were encapsulated in a sulfated p-xylene polymer matrix, and showed high catalytic activities for several C-C coupling reactions (Scheme 13) [154][155][156][157][158].…”

Section: Porous Materialsmentioning

confidence: 99%

Recent Progress of Metal Nanoparticle Catalysts for C–C Bond Forming Reactions

Ohtaka¹

2021

Catalysts

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Over the past few decades, the use of transition metal nanoparticles (NPs) in catalysis has attracted much attention and their use in C–C bond forming reactions constitutes one of their most important applications. A huge variety of metal NPs, which have showed high catalytic activity for C–C bond forming reactions, have been developed up to now. Many kinds of stabilizers, such as inorganic materials, magnetically recoverable materials, porous materials, organic–inorganic composites, carbon materials, polymers, and surfactants have been utilized to develop metal NPs catalysts. This review classified and outlined the categories of metal NPs by the type of support.

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Section: Porous Materialsmentioning

confidence: 99%

Recent Progress of Metal Nanoparticle Catalysts for C–C Bond Forming Reactions

Ohtaka¹

2021

Catalysts

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“…Gold Supported Ruthenium (SARu(0)) 25) We used the PSSO method to produce Ru NPs with low Ru leaching and good recyclability, which could be a good catalyst for liquid-phase combinatorial organic synthesis. We successfully developed self-assembled Au-supported Ru NPs (SARu(0)) catalysts using a combination of the in situ PSSO method and an appropriate reducing agent.…”

Section: Self-assembledmentioning

confidence: 99%

“…This method is conceptually different from conventional NPs-immobilizing methods using solid supports with preformed coordination sites or pores. We also successfully applied the "in situ PSSO method" to prepare other metal NPs catalysis, such as self-assembled Au-supported Ni NPs catalyst (SANi(0)), 24) self-assembled Au-supported Ru NPs catalyst (SARu(0)), 25) and self-assembled Au-supported Fe NPs catalyst (SAFe(II)). 26) 2.…”

Section: Introductionmentioning

confidence: 99%

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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“…We speculated that the self-assembled Pd NPs, which were encapsulated in a sulfated p -xylene polymer matrix, 9 d were formed using in situ metal NP and nanospace simultaneous organization (PSSO), as illustrated in Scheme 2b : (i) the reduction of a high-valence metal source, (ii) growth of transition metal NPs, (iii) growth of a matrix with appropriately sized nanopores, and (iv) encapsulation of the metal NPs in these nanopores. To prepare SARu, 10 SANi, 11 SAFe( ii ), 12 and SAFe(0) 13 ( Scheme 2a ), the PSSO method involves the in situ reduction of a noble metal precursor to produce in situ metal NPs.…”

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confidence: 99%