Safe Removal of the Allyl Protecting Groups of Allyl Esters using a Recyclable, Low‐Leaching and Ligand‐Free Palladium Nanoparticle Catalyst

Takagi, Koji; Fukuda, Hayato; Shuto, Satoshi; Otaka, Akira; Arisawa, Mitsuhiro

doi:10.1002/adsc.201500055

Cited by 23 publications

(10 citation statements)

References 36 publications

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“…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: 90%

“…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: 95%

“…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: −mentioning

confidence: 90%

Section: Liquid-phase Combinatorial Experimentsmentioning

confidence: 95%

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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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“…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%

“…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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Catalytic Transfer Hydrodebenzylation with Low Palladium Loading

Yakukhnov

Ananikov

2019

Adv Synth Catal

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A highly‐efficient catalytic system for hydrodebenzylation reaction is described. The cleavage of O‐benzyl and N‐benzyl protecting groups was performed using an uncommonly low palladium loading (0.02–0.3 mol%; TON up to 5000) in a relatively short reaction time. The approach was used for a variety of substrates including pharmaceutically important precursors, and gram‐scale deprotection reaction was shown. Transfer conditions together with easy‐to‐make Pd/C catalyst are the key features of this debenzylation scheme.magnified image

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Safe Removal of the Allyl Protecting Groups of Allyl Esters using a Recyclable, Low‐Leaching and Ligand‐Free Palladium Nanoparticle Catalyst

Cited by 23 publications

References 36 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

Development of Metal Nanoparticle Catalysis toward Drug Discovery

Catalytic Transfer Hydrodebenzylation with Low Palladium Loading

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