Palladium on Carbon-Catalyzed Suzuki-Miyaura Coupling Reaction Using an Efficient and Continuous Flow System

Hattori, Tomohiro; Tsubone, Aya; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao

doi:10.3390/catal5010018

Cited by 36 publications

(15 citation statements)

References 24 publications

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“…Pd/C, which is simple in preparation and can be easily separated from the reaction mixture, is the most well-known ligandless catalyst [2][3][4][5]. Palladium salts [1,6] can be also attributed to the ligandless catalysts of the Suzuki reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4-Methoxybiphenyl Using Pd-Containing Catalysts Based on Polymeric Matrix of Functionalized Hypercrosslinked Polystyrene

Nikoshvili

Nemygina

Быков

et al. 2015

Bull. Chem. React. Eng. Catal.

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This paper describes synthesis of Pd-containing catalysts of Suzuki cross-coupling based on aminofunctionalized hypercrosslinked polystyrene. The investigation of the influence of a palladium concentration, solvent composition, temperature, type and concentration of base, and a type of a gas phase was carried out. It was shown that the catalyst developed allows achieving conversion of 4-bromoanisole higher than 98% for less than 1 h at mild reaction conditions and in the absence of a phase transfer agent. Catalyst reduction was found to result in formation of small Pd nanoparticles (about 3 nm in diameter) and a large number of Pd clusters, which are highly active in Suzuki-Miyaura cross-coupling (conversion of 4-bromoanisole reached 90.2% for 3 h).

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Section: Introductionmentioning

confidence: 99%

Synthesis of 4-Methoxybiphenyl Using Pd-Containing Catalysts Based on Polymeric Matrix of Functionalized Hypercrosslinked Polystyrene

Nikoshvili

Nemygina

Быков

et al. 2015

Bull. Chem. React. Eng. Catal.

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“…Recently, continuous flow chemistry has been used in efficient Pd/C‐catalyzed Suzuki reactions (Scheme ) . The substrate flows through the catalyst cartridge at a rate of 1 ml/min, and the time required to complete the coupling reaction was only 20 s during a single‐pass of the reaction solution.…”

Section: Activated Carbonmentioning

confidence: 98%

Carbon‐Based Material‐Supported Palladium Nanocatalysts in Coupling Reactions: Discussion on their Stability and Heterogeneity

Zhao

Cao

2020

Applied Organom Chemis

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Scientific interest in carbon‐based materials (CBMs) has grown dramatically over the past few decades. Due to a variety of atomic orbital hybrid forms (sp, sp2 and sp3 hybridization), carbon can form a variety of materials with diverse structures and characteristics. CBMs used as efficient catalyst supports show extensive promise in organic reactions, which is attributed to their structural similarity with organics, large specific surface area, chemical stability, and photocatalytic properties. This review presents the synthesis of CBM‐supported palladium nanocatalysts based on impregnation, template methods, etc. The CBMs include activated carbon (AC), graphene, carbon nanotubes (CNTs), and their functionalized products, as supports for improving the activity and recyclability of simple Pd nanocatalysts. After surveying the literature where these catalysts have been utilized for carbon–carbon coupling reactions, there is a particular emphasis on Suzuki, Heck, and Sonogashira reactions. The catalytic mechanism of these Pd nanocatalysts (surface heterogeneous catalysis or homogeneous catalysis caused by Pd leaching) is discussed in detail, especially the effect of Pd leaching on the stability of the catalyst.

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“…Thus, the ongoing research in this topic is very intensive because there is still much work that needs to be done to improve the catalytic performance of the supported systems. Therefore, many groups are working on supporting Pd nanoparticles onto mesoporous silica [11,12], alumina [13,14], graphene [15,16], modified graphene [17,18], graphene oxide [19], graphite oxide [20], reduced graphene oxide [21], or other carbon-based materials [22], for example, for the development of novel catalytic systems. However, with supported catalysts considerable work still needs to be carried out in order to increase the versatility of the reagents and products of the C-C coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives

et al. 2017

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Heterogeneous recyclable catalysts in Suzuki-Miyaura C-C coupling reactions are of great interest in green chemistry as reusable alternatives to homogeneous Pd complexes. Considering the interesting properties of fluorinated compounds for the pharmaceutical industry, as precursors of novel materials, and also as components of liquid crystalline media, this present study describes the preparation of different fluorinated biphenyl derivatives by Suzuki-Miyaura coupling reactions catalyzed by a heterogeneous system (G-COOH-Pd-10) based on Pd nanoparticles supported onto COOH-modified graphene. The catalytic activity of the hybrid material G-COOH-Pd-10 has been tested in Suzuki-Miyaura C-C coupling reactions observing excellent versatility and good conversion rates in the reactions of phenylboronic acid, 4-vinylphenylboronic acid, 4-carboxyphenylboronic acid, and 4-fluorophenylboronic acid with 1-bromo-4-fluorobenzene. In addition, the influence of the arylbromide has been studied by carrying out reactions of 4-fluorophenylboronic acid with 1-bromo-2-fluorobenzene, 1-bromo-3-fluorobenzene, 1-bromo-4-fluorobenzene, 2-bromo-5-fluorotoluene, and 2-bromo-4-fluorotoluene. Finally, catalyst recyclability tests show a good degree of reusability of the system based on G-COOH-Pd-10 as the decrease in catalytic activity after five consecutive catalytic cycles in the reaction of 1-bromo-4-fluorobenzene with 4-florophenylboronic acid at 48 hours of reaction is lower than 8% while in the case of reactions at three hours the recyclability of the systems is much lower.

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Palladium on Carbon-Catalyzed Suzuki-Miyaura Coupling Reaction Using an Efficient and Continuous Flow System

Cited by 36 publications

References 24 publications

Synthesis of 4-Methoxybiphenyl Using Pd-Containing Catalysts Based on Polymeric Matrix of Functionalized Hypercrosslinked Polystyrene

Synthesis of 4-Methoxybiphenyl Using Pd-Containing Catalysts Based on Polymeric Matrix of Functionalized Hypercrosslinked Polystyrene

Carbon‐Based Material‐Supported Palladium Nanocatalysts in Coupling Reactions: Discussion on their Stability and Heterogeneity

Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives

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