Palladium nanoparticles stabilized by phosphine ligand for aqueous phase room temperature suzuki-Miyaura coupling

Ge, Jiyuan; Jiang, Jian; Yuan, Chenhuan; Zhang, Chaozhi; Liu, Minghua

doi:10.1016/j.tetlet.2017.02.013

Cited by 23 publications

(9 citation statements)

References 36 publications

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“…If water is used as solvent, a stabilizer soluble in water is required and several systems have been reported to date especially for noble metals [18]. In the case of Pd aqueous suspensions, Pd chloride salts are often used as precursors in the presence of water soluble stabilizers like polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyethylene diamine, polystyrene, polyethylene glycol) [19][20][21][22][23], short-and long-chain surfactants [24,25], calixarenes, cyclodextrins [26,27], natural ligand (glucose, starch, proteins) [28][29][30] and P-or P-O-based ligands [31,32]. As for heterogeneous catalysts, the main influencing synthesis parameters are the metal precursor, the solvent, and the stabilizing system.…”

Section: Graphic Abstractmentioning

confidence: 99%

Selective Aerobic Oxidation of Benzyl Alcohols with Palladium(0) Nanoparticles Suspension in Water

et al. 2021

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This study concerns one of the rare applications of a suspension of palladium nanoparticles in water for oxidation reactions. The aqueous suspension containing well dispersed nanoparticles of 3.85 nm was obtained following a straightforward procedure involving the reduction of Na 2 PdCl 4 with NaBH 4 in the presence of PVP as stabilizing agent. In the way of oxidative catalytic valorisation of lignin, the aqueous suspension was directly applied as catalytic medium for the selective oxidation of vanillic alcohol into vanillin (80 °C, O 2 , 1 h) with more than 90% yield. Reusability of the catalytic medium has been demonstrated, acting as "quasi-homogeneous catalyst". More sophisticated lignin-derived substrates like veratryl alcohol and hydrobenzoin gave yields of 50-80% to the respective aldehyde and ketone. In parallel, this as-synthesized suspension was directly used to prepare a Pd/TiO 2 catalyst, the latter showing less efficiency for the catalytic transformations.

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Section: Graphic Abstractmentioning

confidence: 99%

Selective Aerobic Oxidation of Benzyl Alcohols with Palladium(0) Nanoparticles Suspension in Water

et al. 2021

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“…Although Suzuki coupling reactions are among the most useful methods for the synthesis of carbon skeletons, there are still improvements that could be made to render this technique even more effective. It has also been demonstrated that the use of palladium phosphine species ,, is an excellent strategy for Suzuki couplings under very low palladium loadings. However, phosphine ligands are expensive, toxic, and usually hydrophobic and air-sensitive; therefore, cross-coupling reactions under phosphine-free conditions are still an important challenge for researchers. − Recently, different phosphine-free ligands as diverse as N-heterocyclic carbenes, diimines, diamines, and amides have attracted considerable attention as competent ligands for Suzuki reactions.…”

Section: Introductionmentioning

confidence: 99%

“…It has also been demonstrated that the use of palladium phosphine species ,, is an excellent strategy for Suzuki couplings under very low palladium loadings. However, phosphine ligands are expensive, toxic, and usually hydrophobic and air-sensitive; therefore, cross-coupling reactions under phosphine-free conditions are still an important challenge for researchers. − Recently, different phosphine-free ligands as diverse as N-heterocyclic carbenes, diimines, diamines, and amides have attracted considerable attention as competent ligands for Suzuki reactions.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Method for Suzuki Reactions in Aqueous Media

et al. 2018

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Herein, we report the crystal structure and characterization of mono-6-( l -aminopropanol)-deoxy-β-cyclodextrin (L n @β-CD). A highly efficient, in situ generated catalyst, PdCl 2 (L n @β-CD), was synthesized for palladium-catalyzed cross-coupling reactions under mild reaction conditions, and the use of this catalyst in Suzuki cross-couplings was investigated. Low palladium loadings of 0.01 mol % PdCl 2 (L n @β-CD) (Pd accounted for approximately 8.4% of the catalyst by mass) were found to be highly efficient for Suzuki cross-couplings in water and afforded the corresponding biaryl compounds in excellent yields. The catalyst can be recycled and reused.

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“…Therefore, numerous compounds have been synthesized by different research groups to obtain the most effective catalyst in the SMC reaction. [ 34,44–52 ]…”

Section: Discussionmentioning

confidence: 99%

Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

Akkoç

2021

J Chinese Chemical Soc

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This review was designed to give an overview of the significant parameters in Suzuki‐Miyaura coupling (SMC) reactions, which are a powerful tool for the formation of the carbon–carbon (CC) bond. Since the SMC reaction depends on factors such as solvent, base, temperature, time, catalyst amount, substituent in aryl halides, and molar ratios of the substrates, all these parameters should be screened for a successful SMC reaction. After finding the optimum reaction conditions, the SMC reaction's products of boronic acid derivatives with aryl halides can be obtained in high yields.

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Palladium nanoparticles stabilized by phosphine ligand for aqueous phase room temperature suzuki-Miyaura coupling

Cited by 23 publications

References 36 publications

Selective Aerobic Oxidation of Benzyl Alcohols with Palladium(0) Nanoparticles Suspension in Water

Selective Aerobic Oxidation of Benzyl Alcohols with Palladium(0) Nanoparticles Suspension in Water

Highly Efficient Method for Suzuki Reactions in Aqueous Media

Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

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