Palladium-Nanoparticle-Catalyzed 1,7-Palladium Migration Involving C–H Activation, Followed by Intramolecular Amination: Regioselective Synthesis of <i>N</i>1-Arylbenzotriazoles and an Evaluation of Their Inhibitory Activity toward Indoleamine 2,3-Dioxygenase

Takagi, Koji; Al‐Amin, Mohammad; Hoshiya, Naoyuki; Wouters, Johan; Sugimoto, Hiroshi; Shiro, Yoshitsugu; Fukuda, Hayato; Shuto, Satoshi; Arisawa, Mitsuhiro

doi:10.1021/jo5009838

Cited by 44 publications

(24 citation statements)

References 44 publications

(30 reference statements)

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“…As reported in our previous research, [17][18][19][20][21][22][23][24][25][26][27] SAPd absorbs very few organic compounds and can therefore be used in combinatorial synthesis because of its small surface area. It was envisaged that SGlPd would perform in a similar manner to SAPd.…”

Section: Liquid-phase Combinatorial Experimentsmentioning

confidence: 58%

“…Organic materials containing sulfate and xylene as the major ingredients are distributed between the Pd nanoparticles, allowing for the formation of stable high-density PdNPs without condensation. [17][18][19][20][21][22][23][24][25][26][27] The results of the XANES analysis suggest that the oxidized sulfur preserves the structure of the PdNPs in SGlPd as well as SAPd.…”

Section: −mentioning

confidence: 94%

“…Notably, this catalyst exhibited good recyclability properties in all cases with low palladium leaching. [17][18][19][20][21][22][23][24][25][26][27] In 2015, we successfully analyzed the structure of our SAPd catalyst by X-ray absorption fine structure (XAFS) and transmission electron microscopy (TEM) analyses and found that the Au particles in this material simply acted as a solid support for the SAPd membrane. 27) SAPd is now commercially available as a safe, facile, recyclable and low-leaching PdNP catalyst.…”

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confidence: 99%

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Development of a Sulfur-Modified Glass-Supported Pd Nanoparticle Catalyst for Suzuki–Miyaura Coupling

Xiao

Hoshiya

Fujiki

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Liquid-phase Combinatorial Experimentsmentioning

confidence: 58%

Section: −mentioning

confidence: 94%

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confidence: 99%

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Development of a Sulfur-Modified Glass-Supported Pd Nanoparticle Catalyst for Suzuki–Miyaura Coupling

Xiao

Hoshiya

Fujiki

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…92 It should be noted that a molecular oxidant was again required for this transformation, hinting at the involvement of a catalytically relevant Pd II species. 92 It should be noted that a molecular oxidant was again required for this transformation, hinting at the involvement of a catalytically relevant Pd II species.…”

Section: Metal-metal Frameworkmentioning

confidence: 97%

Catalytic C–H bond functionalisation chemistry: the case for quasi-heterogeneous catalysis

2015

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This feature article examines the potential of heterogeneous Pd species to mediate catalytic C-H bond functionalisation processes employing suitable substrates (e.g. aromatic/heteroaromatic compounds). A focus is placed on the reactivity of supported and non-supported Pd nanoparticle (PdNPs) catalysts, in addition to the re-appropriation of well-established heterogeneous Pd catalysts such as Pd/C. Where possible, reasonable comparisons are made between PdNPs and traditional 'homogeneous' Pd precatalyst sources (which form PdNPs). The involvement of higher order Pd species in traditional cross-coupling processes, such as Mizoroki-Heck, Sonogashira and Suzuki-Miyaura reactions, allows the exemplification of potential future topics for study in the area of catalytic C-H bond functionalisation processes.

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“…In this review, we summarize our recently developed novel Pd NPs catalyst, named self-assembled Au-supported palladium (SAPd(0)), which can repeatedly catalyze Suzuki-Miyaura coupling, Buchwald-Hartwig reaction, carbon(sp 2 and sp 3 )hydrogen functionalization, double carbonylation, removal of the allyl protecting groups of allyl esters, and redox switching without any ligand. [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).…”

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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Palladium-Nanoparticle-Catalyzed 1,7-Palladium Migration Involving C–H Activation, Followed by Intramolecular Amination: Regioselective Synthesis of N1-Arylbenzotriazoles and an Evaluation of Their Inhibitory Activity toward Indoleamine 2,3-Dioxygenase

Cited by 44 publications

References 44 publications

Development of a Sulfur-Modified Glass-Supported Pd Nanoparticle Catalyst for Suzuki–Miyaura Coupling

Development of a Sulfur-Modified Glass-Supported Pd Nanoparticle Catalyst for Suzuki–Miyaura Coupling

Catalytic C–H bond functionalisation chemistry: the case for quasi-heterogeneous catalysis

Development of Metal Nanoparticle Catalysis toward Drug Discovery

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