Ligand-free Suzuki–Miyaura coupling reaction of an aryl chloride using a continuous irradiation type microwave and a palladium nanoparticle catalyst: effect of a co-existing solid

Yamada, Makito; Shio, Yasunori; Akiyama, Toshiki; Honma, Tetsuo; Ohki, Yuuta; Takahashi, Naoyuki; Murai, Kenichi; Arisawa, Mitsuhiro

doi:10.1039/c9gc01043b

Cited by 13 publications

(4 citation statements)

References 31 publications

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“…However, from the earliest work, it was suggested that the absence of ligands could significantly enhance the catalytic activity of such surfaces . As such, a number of different approaches to stabilizing naked PdNPs have been taken, and used in Suzuki–Miyaura reactions. − However, given the problems with naked PdNPs agglomerating and/or leaching, there can often be limits to the observed TONs that can be achieved using such systems. , This is distinct from some of the ligand-stabilized Pd nanoparticles discussed in the introduction to this paper. As such, there are clear needs for more effective ways of stabilizing naked PdNPs, and we reason that our gel stabilization strategy reported here is one such way of doing so.…”

Section: Resultsmentioning

confidence: 99%

Mechanically Robust Hybrid Gel Beads Loaded with “Naked” Palladium Nanoparticles as Efficient, Reusable, and Sustainable Catalysts for the Suzuki–Miyaura Reaction

Albino

Burden

Piras

et al. 2023

ACS Sustainable Chem. Eng.

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The increase in demand for Pd and its low abundance pose a significant threat to its future availability, rendering research into more sustainable Pd-based technologies essential. Herein, we report Pd scavenging mechanically robust hybrid gel beads composed of agarose, a polymer gelator (PG), and an active low-molecular-weight gelator (LMWG) based on 1,3:2,4dibenzylidenesorbitol (DBS), DBS-CONHNH 2 . The robustness of the PG and the ability of the LMWG to reduce Pd(II) in situ to generate naked Pd(0) nanoparticles (PdNPs) combine within these gel beads to give them potential as practical catalysts for Suzuki−Miyaura cross-coupling reactions. The optimized gel beads demonstrate good reusability, green metrics, and most importantly the ability to sustain stirring, improving reaction times and energy consumption compared to previous examples. In contrast to previous reports, the leaching of palladium from these next-generation beads is almost completely eliminated. Additionally, for the first time, a detailed investigation of these Pd-loaded gel beads explains precisely how the nanoparticles are formed in situ without a stabilizing ligand. Further, detailed catalytic investigations demonstrate that catalysis occurs within the gel beads. Hence, these beads can essentially be considered as robust "nonligated" heterogeneous PdNP catalysts. Given the challenges in developing ligand-free, naked Pd nanoparticles as stable catalysts, these gel beads may have future potential for the development of easily used systems to perform chemical reactions in "kit" form.

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Section: Resultsmentioning

confidence: 99%

Mechanically Robust Hybrid Gel Beads Loaded with “Naked” Palladium Nanoparticles as Efficient, Reusable, and Sustainable Catalysts for the Suzuki–Miyaura Reaction

Albino

Burden

Piras

et al. 2023

ACS Sustainable Chem. Eng.

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“…Scheme 107 PdNPs/KCC-1 mediated carbonylative SM cross-coupling reaction 223 In 2019, Yamada and co-workers 224 investigated the effect of a co-existing metal in the ligand-free Suzuki-Miyaura coupling reaction of an aryl chloride under continuous irradiation microwave and a PdNPs catalyst (SGlPd), and established that the co-existing metal such as aluminum foil is involved in this reaction due to its microwave absorption ability in the reaction system. Mohazzab and co-workers 225 synthesized reusable mesh-GO/Pd catalyst by immobilization of Pd NPs on stainless-steel mesh.…”

Section: Review Synopenmentioning

confidence: 99%

A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview

Kumar,

Jyoti

et al. 2023

SynOpen

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During the previous couple of decades, transition-metal (Fe, Co, Cu, Ni, Ru, Rh, Pd, Ag, Au) catalyzed inter- and intramolecular coupling reactions have attracted huge attention for the construction of C–C and C–heteroatom (like C–N, C–P, C–O, C–S, etc.) bonds to synthesize a diverse range of polymers, fine chemicals, and agrochemicals (mainly fungicides, herbicides, and insecticides), as well as biologically and pharmaceutically important organic molecules. Furthermore, the employment of lower cost and easily available metals such as first-row transition-metal salts or metal complexes of Fe, Co, Cu, Ni as catalysts compared to the precious metals such as Pd, Ag, Au in cross-coupling reactions have led to major advances in applications within the fields of synthesis. A number of cross-coupling reactions catalyzed by transition metals have been explored, including Suzuki, Heck, Sonogashira, Stille, Kumada, Kochi, Murahashi, Corriu, and Negishi reactions, as well as carbonylative, decarboxylative, reactions and α-arylations. In this review, we offer a comprehensive summary of the cross-coupling reaction catalyzed by different transition metals from the year 2009 to date.1 Introduction2 Pd-Catalyzed Reactions2.1 C–C Cross-Coupling Reactions2.2 C–N Cross-Coupling Reactions2.3 C–P Cross-Coupling Reactions3 Ni-Catalyzed Cross-Coupling Reactions3.1 C–C Cross-Coupling Reactions4 Cu-Catalyzed Cross-Coupling Reactions4.1 C–C Cross-Coupling Reactions4.2 C–O Cross-Coupling Reactions4.2 C–N Cross-Coupling Reactions4.4 C–P Cross-Coupling Reactions4.5 C–Se Cross-Coupling Reactions4.6 C–S Cross-Coupling Reactions5 Fe-Catalyzed Reactions5.1 C–C Cross-Coupling Reactions5.2 C–S Cross-Coupling Reactions6 Co-Catalyzed Reactions7 Transition-Metal Nanoparticle-Promoted Reactions7.1 Pd Nanoparticles7.2 Cu Nanoparticles8 Miscellaneous Reactions9 Perspectives and Future Directions

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“…One of the most fundamental supports for metal NPs is inorganic materials such as metal oxides, clay, and so on [31][32][33]. There have been developed many highly active inorganic materials and supported metal NP catalysts, such as those which proceed the C-C bond forming reaction at room temperature [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51]. Typical recent examples include the following:…”

Section: Several Supports For Metal Nanoparticles 21 Inorganic 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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Ligand-free Suzuki–Miyaura coupling reaction of an aryl chloride using a continuous irradiation type microwave and a palladium nanoparticle catalyst: effect of a co-existing solid

Abstract: A co-existing solid, Al foil, plays a key role in ligand-free Suzuki–Miyaura coupling using SGlPd (sulfur-modified glass-supported Pd) and continuous microwave irradiation.

Cited by 13 publications

References 31 publications

Mechanically Robust Hybrid Gel Beads Loaded with “Naked” Palladium Nanoparticles as Efficient, Reusable, and Sustainable Catalysts for the Suzuki–Miyaura Reaction

Mechanically Robust Hybrid Gel Beads Loaded with “Naked” Palladium Nanoparticles as Efficient, Reusable, and Sustainable Catalysts for the Suzuki–Miyaura Reaction

A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview

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

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