Suzuki–Miyaura coupling under air in water promoted by polymer supported palladium nanoparticles

Dell’Anna, Maria Michela; Mali, Matilda; Mastrorilli, Piero; Rizzuti, Antonino; Ponzoni, Chiara; Leonelli, Cristina

doi:10.1016/j.molcata.2012.09.022

Cited by 45 publications

(22 citation statements)

References 66 publications

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“…The polymer most commonly used to stabilize NPs is poly-(N-vinyl-2-pyrollidone) (PVP), however, many other polymers have been used as well (see, e.g., Refs. [16][17][18][19][20][21][22][23][24]). …”

Section: Nanoparticle Catalysismentioning

confidence: 99%

“…Interest in Pd NPs in catalysis is immense [8,9,[36][37][38], with the SMXR attracting particular interest (see examples in References [21][22][23][24][39][40][41][42][43][44]). Contrary to the situation for the SMXR, reports on the OHR of arylboronic acids catalyzed by Pd NPs are few and far between.…”

Section: The Suzuki-miyaura Cross Coupling Reaction and The Oxidativementioning

confidence: 99%

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Halide-Enhanced Catalytic Activity of Palladium Nanoparticles Comes at the Expense of Catalyst Recovery

et al. 2017

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Abstract:In this communication, we present studies of the oxidative homocoupling of arylboronic acids catalyzed by immobilised palladium nanoparticles in aqueous solution. This reaction is of significant interest because it shares a key transmetallation step with the well-known Suzuki-Miyaura cross-coupling reaction. Additives can have significant effects on catalysis, both in terms of reaction mechanism and recovery of catalytic species, and our aim was to study the effect of added halides on catalytic efficiency and catalyst recovery. Using kinetic studies, we have shown that added halides (added as NaCl and NaBr) can increase the catalytic activity of the palladium nanoparticles more than 10-fold, allowing reactions to be completed in less than half a day at 30 • C. However, this increased activity comes at the expense of catalyst recovery. The results are in agreement with a reaction mechanism in which, under conditions involving high concentrations of chloride or bromide, palladium leaching plays an important role. Considering the evidence for analogous reactions occurring on the surface of palladium nanoparticles under different reaction conditions, we conclude that additives can exert a significant effect on the mechanism of reactions catalyzed by nanoparticles, including switching from a surface reaction to a solution reaction. The possibility of this switch in mechanism may also be the cause for the disagreement on this topic in the literature.

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Section: Nanoparticle Catalysismentioning

confidence: 99%

Section: The Suzuki-miyaura Cross Coupling Reaction and The Oxidativementioning

confidence: 99%

Halide-Enhanced Catalytic Activity of Palladium Nanoparticles Comes at the Expense of Catalyst Recovery

et al. 2017

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“…A C C E P T E D Pd-pol pre-catalyst was successfully employed in several palladium promoted reactions [26,27,28,29,30,31,32,33,34,35]. In all cases, the pristine Pd(II) supported complex was reduced in situ under reaction conditions to Pd(0), forming palladium nanoparticles (NPs) (the real active species) immobilized onto the insoluble support (Pd-pol, Scheme 1) and stabilized by the macroporous and reticulated polymer matrix [36].…”

Section: A N U S C R I P Tmentioning

confidence: 99%

Esterification, transesterification and hydrogenation reactions of polyunsaturated compounds catalyzed by a recyclable polymer supported palladium catalyst

Dell’Anna

Capodiferro

Mali

et al. 2016

Journal of Organometallic Chemistry

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“…On the other hand, metal nanoparticles possess high catalytic activity in water [11][12][13][14][15][16][17][18][19] and have been used not only as semi-heterogeneous catalysts, but also as semi-heterogeneous supports [20][21][22][23]. Unfortunately, heterogenization of metal nanoparticles decreases catalytic activity.…”

Section: Introductionmentioning

confidence: 99%

“…Unfortunately, heterogenization of metal nanoparticles decreases catalytic activity. Additionally, the recovery and reuse of metal nanoparticles have been difficult to achieve due to a significant loss and/or morphology changes of the metal nanoparticles during reaction and workup [13][14][15]. Since leaching of soluble metal species from the support is a major cause of catalyst deactivation, efforts have been reported to develop an effective support that prevents leaching of metal species [16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Application of “Boomerang” Linear Polystyrene-Stabilized Pd Nanoparticles to a Series of C-C Coupling Reactions in Water

et al. 2015

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Abstract:The application of a catch-and-release system for soluble Pd species between water (reaction medium) and polystyrene (polymer support) was examined in the Suzuki coupling reaction with 2-bromothiophene and the Heck reaction with styrene or bromobenzene. Although a slight increase in particle size was observed by TEM after re-stabilization of the Pd species on linear polystyrene, no agglomeration was observed.

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Suzuki–Miyaura coupling under air in water promoted by polymer supported palladium nanoparticles

Cited by 45 publications

References 66 publications

Halide-Enhanced Catalytic Activity of Palladium Nanoparticles Comes at the Expense of Catalyst Recovery

Halide-Enhanced Catalytic Activity of Palladium Nanoparticles Comes at the Expense of Catalyst Recovery

Esterification, transesterification and hydrogenation reactions of polyunsaturated compounds catalyzed by a recyclable polymer supported palladium catalyst

Application of “Boomerang” Linear Polystyrene-Stabilized Pd Nanoparticles to a Series of C-C Coupling Reactions in Water

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