Ligand-free Suzuki–Miyaura coupling using ruthenium(0) nanoparticles and a continuously irradiating microwave system

Akiyama, Toshiki; Taniguchi, Takahisa; Saito, Nozomi; Doi, Ryohei; Honma, Tetsuo; Tamenori, Y.; Ohki, Yuuta; Takahashi, Naoyuki; Fujioka, Hiromichi; Sato, Yoshihiro; Arisawa, Mitsuhiro

doi:10.1039/c7gc01166k

Cited by 31 publications

(23 citation statements)

References 54 publications

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“…While supported Pd catalysts catalyzed the coupling reactions at relatively higher reaction temperature, with more palladium content and prolonged reaction time, which makes the process less efficient. Recently, supported Ru NPs were also investigated for ligand‐free Suzuki‐Miyaura coupling using dimethoxyethane at 80 °C, under microwave irradiation . Borkowski et al.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Highly Active Pd Nanoparticles Supported Iron Oxide Catalyst for Selective Hydrogenation and Cross‐Coupling Reactions in Aqueous Medium

et al. 2019

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Post synthetic approach was successfully employed for the synthesis of Pd supported iron oxide (Pd‐Fe2O3TA) catalyst using polyvinylpyrrolidone as capping agent and triethanolamine as reducing agent. Performance of Pd‐Fe2O3TA catalyst was investigated for selective hydrogenation of nitro compounds and Suzuki coupling reactions. Prepared catalyst exhibited excellent yield of corresponding substituted amines and biphenyls, under optimized reaction conditions. Different analytical techniques such as BET‐surface area measurements, XRD, ICP‐AES, SEM, TEM, XPS, TPR, FT‐IR, RAMAN, UV‐Vis and EXAFS analysis were employed to characterize the catalyst. Average particle size of palladium nanoparticles (NPs) was found to be ∼5.2 nm supported on 60–120 nm size of iron oxide nanocrystals. Various reaction parameters such as time, temperature, solvents, active metal loading, base and different substituent were investigated in detail. Different catalysts were also prepared and compared their activity with that of Pd‐Fe2O3TA catalyst. Experimental observations revealed that size of palladium NPs and metal‐support interaction favoured the superior activity of Pd‐Fe2O3TA catalyst compared to other catalysts. Stability of Pd‐Fe2O3TA catalyst was confirmed by its recyclability tests indicated true heterogeneous nature of catalyst.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Highly Active Pd Nanoparticles Supported Iron Oxide Catalyst for Selective Hydrogenation and Cross‐Coupling Reactions in Aqueous Medium

et al. 2019

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“…Based on its low leaching, our newly developed SGlPd catalyst could also be recycled up to 10 times without any discernible decrease in its catalytic activity. Nickel (SANi(0)) 24) After we obtained the above results, we decided that the in situ PSSO method could be used to immobilize various transition-metal NPs, including base metals. Our in situ PSSO method can be used easily to produce Ni NPs with low Ni leaching and good recyclability for use in organic synthesis.…”

Section: Liquid-phase Combinatorial Experimentsmentioning

confidence: 99%

“…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). As a consequence, we found that SAPd(0) has approximately ten layers of self-assembled Pd(0) NPs, a size of less than 5 nm, on Au surface.…”

Section: Introductionmentioning

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%

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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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“…The power of nano—catalysts is proved by their frequent applications in various transformations like oxygen reduction, water oxidation, oxidation of cyclohexenone to phenol, hydrogen generation from formic acid, ultrafast coupling of aryllithium reagents with aryl bromides, Se–Se bond activation, C–O bond activation, one–pot conversion of nitro phenol to benzoxazole, CuAAc reactions, Suzuki–Miyaura coupling, alkyne–cis–semihydrogenation, A 3 –coupling, peptide bond formation, acceptorless dehydrogenative aromatization, selective alcohol oxidation, aerobic oxidation of diaryl and aryl(hetero) methylenes,and C–H bond activation. In spite of these valuable catalytic properties of nanoparticles, there is a significant amount of research is needed to develop methods using economic, cost–effective and readily available non–noble metal nano catalysts.…”

Section: Introductionmentioning

confidence: 99%

A New Avenue to the Synthesis of Symmetrically Substituted Pyridines Catalyzed by Magnetic Nano–Fe₃O₄: Methyl Arenes as Sustainable Surrogates of Aryl Aldehydes

et al. 2019

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Ligand-free Suzuki–Miyaura coupling using ruthenium(0) nanoparticles and a continuously irradiating microwave system

Abstract: A good combination between a continuously irradiating microwave system and recyclable Ru(0) nanoparticle for ligand-free Suzuki–Miyaura coupling.

Cited by 31 publications

References 54 publications

Synthesis of Highly Active Pd Nanoparticles Supported Iron Oxide Catalyst for Selective Hydrogenation and Cross‐Coupling Reactions in Aqueous Medium

Synthesis of Highly Active Pd Nanoparticles Supported Iron Oxide Catalyst for Selective Hydrogenation and Cross‐Coupling Reactions in Aqueous Medium

Development of Metal Nanoparticle Catalysis toward Drug Discovery

A New Avenue to the Synthesis of Symmetrically Substituted Pyridines Catalyzed by Magnetic Nano–Fe₃O₄: Methyl Arenes as Sustainable Surrogates of Aryl Aldehydes

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Ligand-free Suzuki–Miyaura coupling using ruthenium(0) nanoparticles and a continuously irradiating microwave system

Abstract: A good combination between a continuously irradiating microwave system and recyclable Ru(0) nanoparticle for ligand-free Suzuki–Miyaura coupling.

Cited by 31 publications

References 54 publications

Synthesis of Highly Active Pd Nanoparticles Supported Iron Oxide Catalyst for Selective Hydrogenation and Cross‐Coupling Reactions in Aqueous Medium

Synthesis of Highly Active Pd Nanoparticles Supported Iron Oxide Catalyst for Selective Hydrogenation and Cross‐Coupling Reactions in Aqueous Medium

Development of Metal Nanoparticle Catalysis toward Drug Discovery

A New Avenue to the Synthesis of Symmetrically Substituted Pyridines Catalyzed by Magnetic Nano–Fe3O4: Methyl Arenes as Sustainable Surrogates of Aryl Aldehydes

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A New Avenue to the Synthesis of Symmetrically Substituted Pyridines Catalyzed by Magnetic Nano–Fe₃O₄: Methyl Arenes as Sustainable Surrogates of Aryl Aldehydes